Name: synthesis and characterization of 1,2-dithiolane modified self-assembling peptides
Uploaded: 2018-08-20T13:00:00
Description: Watch this Scientific Journal Video about Synthesis and Characterization of 1,2-Dithiolane Modified Self-Assembling Peptides at JoVE.com

Los autores desean agradecer al Dr. B. Ellen Scanley su capacitación técnica y ayuda usar la temperatura en el centro de la Universidad (CSCU) y universidades del estado de Connecticut para nanotecnología y Dr. Ishita Mukerji en Universidad de Wesleyan para tener acceso a su CD Espectrofotómetro. El trabajo divulgado fue apoyado en parte por el Instituto de Ciencias en la Universidad de Fairfield, Connecticut NASA espacio Grant consorcio y por la National Science Foundation bajo la beca número-1624774.

1. síntesis y purificación de 1, 2-Dithiolane péptido modificado
<ol><li>Síntesis del precursor dithiolane, 3-(acetylthio) -2-(acetylthiomethyl) propanoico ácido19.
	<ol>
<li>Añadir 1 g de 3-bromo - 2-(bromometil) ácido propiónico (1 equivalente) disuelto en una cantidad mínima de 1 M NaOH (aproximadamente 4 mL) a un matraz de reacción de fondo redondo de 25 mL con agitación a 55 ° C. Tapar el matraz de reacción con un septo y bajo atmósfera de nitrógeno.</li>
		<...

<ol>
	<li>Wang, J., Liu, K., Xing, R., Yan, X. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Peptide+self-assembly:+Thermodynamics+and+kinetics.">Peptide self-assembly: Thermodynamics and kinetics.</a> Chemical Society Reviews. 45, 5589-5604 (2016).</li><li>Dong, R., et al. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Functional+supramolecular+polymers+for+biomedical+applications.">Functional supramolecular polymers for biomedical applications.</a> Advanced Materials. 27, 498-526 (2015).</li><li>Edwards-Gayle, C. J. C., Hamley, I. W. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Self-assembly+of+bioactive+peptides,+peptide+conjugates,+and+peptide+mimetic+materials.">Self-assembly of bioactive peptides, peptide conjugates, and peptide mimetic materials.</a> Organic and Biomolecular Chemistry. 15, 5867-5876 (2017).</li><li>Goor, O. J. G. M., Hendrikse, S. I. S., Dankers, P. Y. W., Meijer, E. W. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=From+supramolecular+polymers+to+multi-component+biomaterials.">From supramolecular polymers to multi-component biomaterials.</a> Chemical Society Reviews. 46, 6621-6637 (2017).</li><li>DiMaio, J. T. M., Doran, T. M., Ryan, D. M., Raymond, D. M., Nilsson, B. L. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Modulating+supramolecular+peptide+hydrogel+viscoelasticity+using+biomolecular+recognition.">Modulating supramolecular peptide hydrogel viscoelasticity using biomolecular recognition.</a> Biomacromolecules. 18, 3591-3599 (2017).</li><li>DiMaio, J. T. M., Raymond, D. M., Nilsson, B. L. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Display+of+functional+proteins+on+supramolecular+peptide+nanofibrils+using+a+split-protein+strategy.">Display of functional proteins on supramolecular peptide nanofibrils using a split-protein strategy.</a> Organic and Biomolecular Chemistry. 15, 5279-5283 (2017).</li><li>Mahmoud, Z. N., Gunnoo, S. B., Thomson, A. R., Fletcher, J. M., Woolfson, D. N. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Bioorthogonal+dual+functionalization+of+self-assembling+peptide+fibers.">Bioorthogonal dual functionalization of self-assembling peptide fibers.</a> Biomaterials. 32, 3712-3720 (2011).</li><li>Petkau-Milroy, K., Uhlenheuer, D. A., Spiering, A. J. H., Vekemans, J. A. J. M., Brunsveld, L. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Dynamic+and+bio-orthogonal+protein+assembly+along+a+supramolecular+polymer.">Dynamic and bio-orthogonal protein assembly along a supramolecular polymer.</a> Chemical Science. 4, 2886-2891 (2013).</li><li>Li, A., et al. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Neurofibrillar+tangle+surrogates:+Histone+H1+binding+to+patterned+phosphotyrosine+peptide+nanotubes.">Neurofibrillar tangle surrogates: Histone H1 binding to patterned phosphotyrosine peptide nanotubes.</a> Biochemistry. 53, 4225-4227 (2014).</li><li>Sadownik, A., Stefely, J., Regen, S. L. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Polymerized+liposomes+formed+under+extremely+mild+conditions.">Polymerized liposomes formed under extremely mild conditions.</a> Journal of the American Chemical Society. 108, 7789-7791 (1986).</li><li>Zhang, N., et al. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=ATN-161+Peptide+functionalized+reversibly+cross-linked+polymersomes+mediate+targeted+doxorubicin+delivery+into+melanoma-bearing+C57BL/6+mice.">ATN-161 Peptide functionalized reversibly cross-linked polymersomes mediate targeted doxorubicin delivery into melanoma-bearing C57BL/6 mice.</a> Molecular Pharmaceutics. 14, 2538-2547 (2017).</li><li>Margulis, K., et al. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Formation+of+polymeric+nanocubes+by+self-assembly+and+crystallization+of+dithiolane-containing+triblock+copolymers.">Formation of polymeric nanocubes by self-assembly and crystallization of dithiolane-containing triblock copolymers.</a> Angewandte Chemie International Edition. 56, 16357-16362 (2017).</li><li>Zhang, X., Waymouth, R. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=1,2-Dithiolane-Derived+Dynamic,+Covalent+Materials:+Cooperative+Self-Assembly+and+Reversible+Cross-Linking.">1,2-Dithiolane-Derived Dynamic, Covalent Materials: Cooperative Self-Assembly and Reversible Cross-Linking.</a> Journal of the American Chemical Society. 139, 3822-3833 (2017).</li><li>Sakia, N., Matile, S. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Stack+exchange+strategies+for+the+synthesis+of+covalent+double-channel+photosystems+by+self-organizing+surface-initiated+polymerization.">Stack exchange strategies for the synthesis of covalent double-channel photosystems by self-organizing surface-initiated polymerization.</a> Journal of the American Chemical Society. 133, 18542-18545 (2011).</li><li>Uji, H., Morita, T., Kimura, S. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Molecular+direction+dependence+of+single-molecule+conductance+of+a+helical+peptide+in+molecular+junction.">Molecular direction dependence of single-molecule conductance of a helical peptide in molecular junction.</a> Physical Chemistry Chemical Physics. 15, 757-760 (2013).</li><li>Liang, C., Ni, R., Smith, J. E., Childers, W. S., Mehta, A. K., Lynn, D. G. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Kinetic+intermediates+in+amyloid+assembly.">Kinetic intermediates in amyloid assembly.</a> Journal of the American Chemical Society. 136, 15116-15149 (2014).</li><li>Smith, J. E., et al. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Defining+the+dynamic+conformational+network+of+cross-&#946;+peptide+assembly.">Defining the dynamic conformational network of cross-&#946; peptide assembly.</a> Israel Journal of Chemistry. 55, 763-769 (2015).</li><li>Black, S. P., Sanders, J. K. M., Stefankiewicz, A. R. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Disulfide+exchange:+Exposing+supramolecular+reactivity+through+dynamic+covalent+chemistry.">Disulfide exchange: Exposing supramolecular reactivity through dynamic covalent chemistry.</a> Chemical Society Reviews. 43, 1861-1872 (2014).</li><li>Vendetti, A., et al. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Dihydroasparagusic+acid:+Antioxidant+and+tyrosinase+inhibitory+activities+and+improved+synthesis.">Dihydroasparagusic acid: Antioxidant and tyrosinase inhibitory activities and improved synthesis.</a> Journal of Agricultural and Food Chemistry. 61, 6848-6855 (2013).</li><li>Stawikowski, M., Fields, G. B. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Introduction+to+peptide+synthesis.">Introduction to peptide synthesis.</a> Current Protocols in Protein Science. 26, (2002).</li><li>Canadell, J., Goossens, H., Klumperman, B. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Self-healing+materials+based+on+disulfide+links.">Self-healing materials based on disulfide links.</a> Macromolecules. 44, 2536-2541 (2011).</li><li>Lafont, U., van Zeijl, H., van der Zwaag, S. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Influence+of+cross-linkers+on+the+cohesive+and+adhesive+self-healing+ability+of+polydisulfide-based+thermosets.">Influence of cross-linkers on the cohesive and adhesive self-healing ability of polydisulfide-based thermosets.</a> ACS Applied Materials and Interfaces. 4, 6280-6288 (2012).</li><li>Komaromy, D., Stuart, M. C. A., Santiago, G. M., Tezcan, M., Krasnikov, V. V., Otto, S. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Self-assembly+can+direct+dynamic+covalent+bond+formation+toward+diversity+or+specificity.">Self-assembly can direct dynamic covalent bond formation toward diversity or specificity.</a> Journal of the American Chemical Society. 139, 6234-6241 (2017).</li><li>McAvery, K. M., Guan, B., Fortier, C. A., Tarr, M. A., Cole, R. B. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Laser-induced+oxidation+of+cholesterol+observed+during+MALDI-TOF+mass+spectrometry.">Laser-induced oxidation of cholesterol observed during MALDI-TOF mass spectrometry.</a> Journal of the American Society for Mass Spectrometry. 22, 659-669 (2011).</li><li>Krimm, S., Bandekar, J. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Vibrational+spectroscopy+and+conformation+of+peptides,+polypeptides,+and+proteins.">Vibrational spectroscopy and conformation of peptides, polypeptides, and proteins.</a> Advances in Protein Chemistry. 38, 181-364 (1986).</li><li>Halverson, K. J., Sucholeiki, I., Ashburn, T. T., Lansbury, P. T. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Location+of+&#946;-sheet-forming+sequences+in+amyloid+proteins+by+FTIR.">Location of &#946;-sheet-forming sequences in amyloid proteins by FTIR.</a> Journal of the American Chemical Society. 113, 6701-6703 (1991).</li><li>Greenfield, N., Fasman, G. D. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Computed+circular+dichroism+spectra+for+the+evaluation+of+protein+confirmation.">Computed circular dichroism spectra for the evaluation of protein confirmation.</a> Biochemistry. 8, 4108-4116 (1969).</li><li>. ImageJ Available from: <a target="_blank" href="https://imagej.nih.gov/ij">https://imagej.nih.gov/ij</a> (2016)</li><li>Roy, S., Shinde, S., Hamilton, G. A., Hartnett, H. E., Jones, A. K. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Artificial+[FeFe]-hydrogenase:+On+resin+modification+of+an+amino+acid+to+anchor+a+hexacarbonyldiiron+cluster+in+a+peptide+framework.">Artificial [FeFe]-hydrogenase: On resin modification of an amino acid to anchor a hexacarbonyldiiron cluster in a peptide framework.</a> European Journal of Inorganic Chemistry. 2011, 1050-1055 (2011).</li><li>Van Duinen, S. G., Castano, E. M., Prelli, F., Bots, G. T. A. B., Luyendijk, W., Frangione, B. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Hereditary+cerebral+hemorrhage+with+amyloidosis+in+patients+of+Dutch+origin+is+related+to+Alzheimer+disease.">Hereditary cerebral hemorrhage with amyloidosis in patients of Dutch origin is related to Alzheimer disease.</a> Proceedings of the National Academy of Sciences of the United States of America. 84, 5991-5994 (1987).</li><li>Barth, A. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=The+infrared+absorption+of+amino+acid+sidechains.">The infrared absorption of amino acid sidechains.</a> Progress in Biophysics and Molecular Biology. 74, 141-173 (2000).</li><li>Jayaraman, M., et al. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Slow+amyloid+nucleation+via+&#945;-helix-rich+oligomeric+intermediates+in+short+polyglutamine-containing+Huntingtin+fragments.">Slow amyloid nucleation via &#945;-helix-rich oligomeric intermediates in short polyglutamine-containing Huntingtin fragments.</a> Journal of Molecular Biology. 415, 881-899 (2012).</li></ol>

Este artículo discute los detalles de la síntesis y la purificación de un peptide uno mismo-montaje N-terminal 1, 2-dithiolane modificado y la caracterización de las estructuras supramoleculares resultantes. La síntesis del péptido 1, 2-dithiolane divulgado aquí tiene las ventajas, incluyendo una síntesis de un solo paso para producir el precursor dithiolane, 3-(acetylthio) -2-(acetylthiomethyl) propanoico ácido y la resina en microondas reacción de desprotección de la precursor thioacetate protección de grup...

El enlace peptídico sólido formación química implicada en síntesis del peptide de la fase sólida y la capacidad para controlar la composición y la longitud de la secuencia hacen los péptidos que uno mismo-montan en estructuras supramoleculares un campo muy investigado. Los factores que controlan y estabilizan péptido uno mismo-montado estructuras, incluyendo cadena lateral estérico e interacciones electrostáticas, hidrógeno y efectos hidrofóbicos1, servir como un conjunto de reglas de diseño. Como la investigación en estas reglas de diseño fundamental continúa progresando, el siguiente paso lógico en péptido autoensamblaje implica ampliar la diversidad de funciones y estructuras de péptidos. Mientras que uno mismo-montaje de péptidos es un biomaterial versátil que se han utilizado para muchas aplicaciones biomédicas templando el péptido secuencia o conjunto de condiciones2,3,4, el desarrollo de estrategias para la Asamblea modificaciones a péptido nanofibras en5,6,7,8,9 sigue siendo un área relativamente inexplorada.
Química intercambio y tiol disulfuro dinámicos en la superficie de estructuras supramoleculares es un área que tiene el potencial para producir biomateriales nuevos y funcionales. La incorporación de moléculas de 1, 2-dithiolane (comúnmente un derivado de ácido lipoico (la) o ácido asparagusic (aa)) se han divulgado en liposomas sistemas10,11, bloque copolímeros12,13y como Organización de anclajes en superficies14,15. Adjunto, divulgamos la síntesis y caracterización de un peptide uno mismo-montaje derivado del núcleo nucleating del péptido Aβ asociado con la enfermedad de Alzheimer que es modificada en el N-terminal con 1, 2-dithiolane grupo funcional16, 17. Las fibras supramoleculares que ahora sirven como una plataforma experimental para el estudio de la reactividad en la superficie supramolecular de fibras amiloides18intercambio de disulfuro y tiol.

<table>
	<tbody>
		<tr>
			<td>Rink amide MBHA resin, high load</td>
			<td>Gyros Protein Technologies</td>
			<td>RAM-5-HL</td>
			<td>Avoid contact with skin and eyes; do not inhale</td>
		</tr>
		<tr>
			<td>N,N-Dimethylformamide</td>
			<td>Fisher Scientific</td>
			<td>D119-4</td>
			<td>Flammable liquid and vapor; irritating to eyes and skin; Use personal protective equipment; keep away from open flame</td>
		</tr>
		<tr>
			<td>Fmoc-L-Val-OH</td>
			<td>Gyros Protein Technologies</td>
			<td>FLA-25-V</td>
			<td>Wear personal protective equipment; do not inhale</td>
		</tr>
		<tr>
			<td>Fmoc-L-Leu-OH</td>
			<td>Gyros Protein Technologies</td>
			<td>FLA-25-L</td>
			<td>Wear personal protective equipment; do not inhale</td>
		</tr>
		<tr>
			<td>Fmoc-L-Lys(Boc)-OH</td>
			<td>Gyros Protein Technologies</td>
			<td>FLA-25-KBC</td>
			<td>Wear personal protective equipment; do not inhale</td>
		</tr>
		<tr>
			<td>Fmoc-L-Phe-OH</td>
			<td>Gyros Protein Technologies</td>
			<td>FLA-25-F</td>
			<td>Wear personal protective equipment; do not inhale</td>
		</tr>
		<tr>
			<td>Fmoc-L-Ala-OH</td>
			<td>Gyros Protein Technologies</td>
			<td>FLA-25-A</td>
			<td>Wear personal protective equipment; do not inhale</td>
		</tr>
		<tr>
			<td>Fmoc-L-Gln(Trt)-OH</td>
			<td>Gyros Protein Technologies</td>
			<td>FLA-25-QT</td>
			<td>Wear personal protective equipment; do not inhale</td>
		</tr>
		<tr>
			<td>N,N,N&#8242;,N&#8242;-Tetramethyl-O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate</td>
			<td>Gyros Protein Technologies</td>
			<td>26432</td>
			<td>Causes skin, eye and respiratory irritation; do not inhale; use under hood or in well ventilated area</td>
		</tr>
		<tr>
			<td>0.4 M N-methylmorpholine in DMF</td>
			<td>Gyros Protein Technologies</td>
			<td>PS3-MM-L</td>
			<td>highly flammable; wear personal protective equipment; keep away from heat and keep container tightly closed; do not inhale or swallow; wash skin thoroughly after handling</td>
		</tr>
		<tr>
			<td>20% piperidine in DMF</td>
			<td>Gyros Protein Technologies</td>
			<td>PS3-PPR-L</td>
			<td>Causes severe eye and skin burns; Flammable Liquid and vapor; Do not inhale</td>
		</tr>
		<tr>
			<td>dichloromethane</td>
			<td>Fisher Scientific</td>
			<td>D37-4</td>
			<td>May cause cancer; Do not inhale; Wear personal protective equipment; use under hood only; if contacted rise with water for at least 15 minutes and obtain medical attention</td>
		</tr>
		<tr>
			<td>acetonitrile</td>
			<td>Fisher Scientific</td>
			<td>A998-4</td>
			<td>Flammable; irritating to eyes; Use personal protective equipment; Use only under a fume hood; keep away from open flame or hot surface; if contacted rinse wiith water for at least 15 minutes and obtain medical attention</td>
		</tr>
		<tr>
			<td>trifluoroacetic acid</td>
			<td>Fisher Scientific</td>
			<td>A116-50</td>
			<td>Causes severe burns; do not inhale; harmful to aquatic life; use personal protective equipment; use only under fume hood; if contacted rinse with water for at least 15 minutes and obain immediate medical attention</td>
		</tr>
		<tr>
			<td>4% uranyl acetate</td>
			<td>Electron Microscopy Sciences</td>
			<td>22400-4</td>
			<td>Do not inhale; harmful to aquatic life</td>
		</tr>
		<tr>
			<td>4-(2-Hydroxyethyl)piperazine-1-ethanesulfonic acid</td>
			<td>Acros Organics</td>
			<td>AC172571000</td>
			<td>Do not inhale; use outdoors or in well-ventilated area</td>
		</tr>
		<tr>
			<td>nitrogen Gas</td>
			<td>TechAir</td>
			<td></td>
			<td>Contents under pressure, may explode if heated</td>
		</tr>
		<tr>
			<td>3-bromo-2-(bromomethyl)propionic acid</td>
			<td>Alfa Aesar</td>
			<td>AAA1963014</td>
			<td>Do not inhale; causes irritation to skin and eyes; corrosive</td>
		</tr>
		<tr>
			<td>sodium hydroxide</td>
			<td>Fisher Scientific</td>
			<td>S318-100</td>
			<td>Use personal protective equipment; use only under fume hood; if contact rinse area for at least 15 minutes and obtain medical attention</td>
		</tr>
		<tr>
			<td>potassium thioacetate</td>
			<td>Acros Organics</td>
			<td>AC221300250</td>
			<td>Causes skin and eye irritation; do not inhale; use personal protective equipment</td>
		</tr>
		<tr>
			<td>sulfuric acid</td>
			<td>Fisher Scientific</td>
			<td>SA213</td>
			<td>Causes burns; keep away from water; keep away from combustible material; do not inhale; use personal protective equipment; if contact rinse area for at least 15 minutes and obtain medical attention</td>
		</tr>
		<tr>
			<td>chloroform-d</td>
			<td>Acros Organics</td>
			<td>AC320690075</td>
			<td>Possible cancer hazard; irritating to skin and eyes; do not inhale; Use personal protective equipment; use only under fume hood; If contact rinse area for at least 15 minutes and obtain medical attention</td>
		</tr>
		<tr>
			<td>chloroform</td>
			<td>Fisher Scientific</td>
			<td>C298-4</td>
			<td>Possible cancer hazard; irritating to skin and eyes; do not inhale; Use personal protective equipment; use only under fume hood; If contact rinse area for at least 15 minutes and obtain medical attention</td>
		</tr>
		<tr>
			<td>N,N-diisopropylethylamine</td>
			<td>Acros Organics</td>
			<td>AC367841000</td>
			<td>Highly flammable; harmful to aquatic life; wear personal protective equipment; do not swallow</td>
		</tr>
		<tr>
			<td>ammonium hydroxide</td>
			<td>Fisher Scientific</td>
			<td>A669S-500</td>
			<td>Corrosive; do not inhale</td>
		</tr>
		<tr>
			<td>methanol</td>
			<td>Fisher Scientific</td>
			<td>A452-4</td>
			<td>Flammable liquid and vapor; use personal protective equipment; do not inhale; If contact rinse area for at least 15 minutes and obtain medical attention</td>
		</tr>
		<tr>
			<td>triisopropylsilane</td>
			<td>Sigma Aldrich</td>
			<td>233781</td>
			<td>Flammable; use personal proctective safety equipment; keep container tightly closed</td>
		</tr>
		<tr>
			<td>diethyl ether</td>
			<td>Fisher Scientific</td>
			<td>E138-1</td>
			<td>Extremely flammable; Irritating to skin and eyes; Use personal protective equipment</td>
		</tr>
		<tr>
			<td>2,5-dihydroxybenzoic acid</td>
			<td>Sigma Aldrich</td>
			<td>39319-10x10MG-F</td>
			<td>do not inhale; irritating to skin and eyes</td>
		</tr>
		<tr>
			<td>alpha-cyano-4-hydroxycinnamic acid</td>
			<td>Alfa Aesar</td>
			<td>AAJ67635EXK</td>
			<td></td>
		</tr>
		<tr>
			<td>c18 zip-tip</td>
			<td>Millipore</td>
			<td>ZTC18S096</td>
			<td></td>
		</tr>
		<tr>
			<td>tris(2-carboxyethyl) phospine hydrochloride</td>
			<td>Thermo Scientific</td>
			<td>PI20490</td>
			<td></td>
		</tr>
		<tr>
			<td>silica gel 60 F254 coated aluminum-backed TLC sheets</td>
			<td>EMD Millipore</td>
			<td>1.05549.0001</td>
			<td></td>
		</tr>
		<tr>
			<td>Thin walled Precision NMR tubes</td>
			<td>Bel-Art</td>
			<td>663000585</td>
			<td>5mm O.D.</td>
		</tr>
		<tr>
			<td>All-plastic Norm-Ject syringes</td>
			<td>Air Tite</td>
			<td>AL10</td>
			<td></td>
		</tr>
		<tr>
			<td>single-use needle</td>
			<td>BD PrecisionGlide</td>
			<td>BD 305185</td>
			<td>used needles get disposed on in sharps waste container</td>
		</tr>
		<tr>
			<td>disposable fritted syringe</td>
			<td>Torviq</td>
			<td>SF1000LL</td>
			<td>10mL fritted syringes were used in the report, but larger syringes are avaibale if needed for larger scale synthesis.</td>
		</tr>
		<tr>
			<td>carbon grid</td>
			<td>Ted Pella, Inc.</td>
			<td>CF200-CU</td>
			<td>Make sure to prepare samples and staining on the carbon grid side, not the shiny copper side of grid</td>
		</tr>
		<tr>
			<td>self-closing tweezers</td>
			<td>Electron Microscopy Sciences</td>
			<td>78318-3X</td>
			<td>very sharp tips, length: 120 mm</td>
		</tr>
		<tr>
			<td>0.1 mm short path length cell</td>
			<td>Starna Cells, Inc.</td>
			<td>20/C-Q-0.1</td>
			<td>Fragile</td>
		</tr>
		<tr>
			<td>10mL Vessel Caps</td>
			<td>CEM</td>
			<td>909210</td>
			<td></td>
		</tr>
		<tr>
			<td>10mL Pressure Vessels</td>
			<td>CEM</td>
			<td>908035</td>
			<td></td>
		</tr>
		<tr>
			<td>Aeris Semi-Prep HPLC column</td>
			<td>Phenomenex</td>
			<td>00F-4632-N0</td>
			<td>150 x 10mm</td>
		</tr>
		<tr>
			<td>cell holder</td>
			<td>Starna Cells, Inc.</td>
			<td>CH-2049</td>
			<td>Needed when using short pathlength cells</td>
		</tr>
		<tr>
			<td>PS3 peptide synthesizer</td>
			<td>Gyros Protein Technologies</td>
			<td></td>
			<td></td>
		</tr>
		<tr>
			<td>DiscoverSP Microwave Reactor</td>
			<td>CEM</td>
			<td></td>
			<td></td>
		</tr>
		<tr>
			<td>centrifuge</td>
			<td>HERMLE</td>
			<td>Z 206 A</td>
			<td>used a fixed 6x50 mL rotor</td>
		</tr>
		<tr>
			<td>HPLC</td>
			<td>Shimadzu</td>
			<td></td>
			<td>UV Detector</td>
		</tr>
		<tr>
			<td>nuclear magnetic resonance spectrometer</td>
			<td>Avance, Bruker</td>
			<td></td>
			<td>300 MHz</td>
		</tr>
		<tr>
			<td>MALDI-TOF mass spectrometer</td>
			<td>Axima Confidence, Shimadzu</td>
			<td></td>
			<td></td>
		</tr>
		<tr>
			<td>lyophilizer</td>
			<td>Millrock Technology</td>
			<td>BT85A</td>
			<td></td>
		</tr>
		<tr>
			<td>Fourier-Transform Infrared Spectrometer</td>
			<td>Alpha Tensor, Bruker</td>
			<td></td>
			<td></td>
		</tr>
		<tr>
			<td>Transmission Electron Microscope</td>
			<td>Tecnai Spirit, FEI</td>
			<td></td>
			<td>Used with Gatan Orius Fiberoptic CCD digital camera. Accessed at CSCU Center for Nanotechnology</td>
		</tr>
		<tr>
			<td>Circular Dichroism Spectropolarimeter</td>
			<td>J-810, JASCO</td>
			<td></td>
			<td>Used with a six-cell Peltier temperature controller. Accessed at Wesleyan University.</td>
		</tr>
	</tbody>
</table>

synthesis and characterization of 1,2-dithiolane modified self-assembling peptides

Este informe se centra en la síntesis de un N-terminal 1, 2-dithiolane modificado peptide uno mismo-montaje y la caracterización de la resultante uno mismo-montar estructuras supramoleculares. La ruta sintética aprovecha la síntesis de péptidos de fase sólida con el acoplamiento en la resina de la molécula del precursor dithiolane, 3-(acetylthio) -2-(acetylthiomethyl) propanoico ácido y la thioacetate asistida por microondas deprotection del péptido N-terminal antes de la división final de la resina para dar 1, 2-dithiolane modificado péptido. Después de la purificación de la cromatografía líquida de alto rendimiento (HPLC) del péptido 1, 2-dithiolane, derivado de la base nucleating del péptido Aβ asociado con la enfermedad de Alzheimer, el péptido aparece uno mismo-montar en fibras amiloideas Cruz-β. Protocolos para la caracterización de las fibras amiloides por espectroscopia infrarroja de Fourier (FT-IR), espectroscopía de dicroísmo circular (CD) y microscopía electrónica de transmisión (TEM) se presentan. Ahora pueden explorar los métodos de modificación de la N-terminal con una molécula de 1, 2-dithiolane a péptidos uno mismo-montaje bien caracterizados como sistemas modelo para desarrollar estrategias de modificación de la Asamblea y explorar la química covalente dinámica en superficies de nanofibras de péptido supramolecular.

Aparte de la síntesis de un paso inicial de la molécula del precursor dithiolane, el resto de la síntesis del péptido 1, 2-dithiolane modificado se realiza en soporte sólido (figura 1A). La conversión de 3-bromo - 2-(bromometil) ácido propiónico para 3-(acetylthio) -2-(acetylthiomethyl) propanoico ácido dithiolane precursor, es confirmado por 1H y 13C NMR (figura 1B y C) antes de qu...

Watch this Scientific Journal Video about Synthesis and Characterization of 1,2-Dithiolane Modified Self-Assembling Peptides at JoVE.com

Synthesis and Characterization of 1,2-Dithiolane Modified Self-Assembling Peptides

Un protocolo para la síntesis de un 1, 2-dithiolane modificada de péptidos y la caracterización de las estructuras supramoleculares resultantes del peptide uno mismo-Asamblea.

Síntesis y caracterización de 1, 2-Dithiolane modifican uno mismo-montaje de péptidos

This report focuses on the synthesis of an N-terminus 1,2-dithiolane modified self-assembling peptide and the characterization of the resulting ...

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