通过树脂上重氮转移反应制备富含叠氮化物的肽。
Azide-rich peptides via an on-resin diazotransfer reaction.
作者信息
Marine Jeannette E, Liang Xiaoli, Song Shuang, Rudick Jonathan G
机构信息
Department of Chemistry, Stony Brook University, Stony Brook, NY, 11794-3400.
出版信息
Biopolymers. 2015 Jul;104(4):419-26. doi: 10.1002/bip.22634.
Abstract
Azide-containing amino acids are valuable building blocks in peptide chemistry, because azides are robust partners in several bioorthogonal reactions. Replacing polar amino acids with apolar, azide-containing amino acids in solid-phase peptide synthesis can be tricky, especially when multiple azide residues are to be introduced in the amino acid sequence. We present a strategy for effectively incorporating multiple azide-containing residues site-specifically.
摘要
含叠氮基的氨基酸是肽化学中有价值的构建单元，因为叠氮化物在几种生物正交反应中是稳定的反应伙伴。在固相肽合成中用非极性的含叠氮基氨基酸取代极性氨基酸可能具有挑战性，尤其是当要在氨基酸序列中引入多个叠氮基残基时。我们提出了一种策略，可有效地将多个含叠氮基的残基位点特异性地掺入。
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1
Helical peptide-foldamers having a chiral five-membered ring amino acid with two azido functional groups.
J Org Chem. 2014 Oct 3;79(19):9125-40. doi: 10.1021/jo501493x. Epub 2014 Sep 16.
2
Drug conjugation to cyclic peptide-polymer self-assembling nanotubes.
Chemistry. 2014 Sep 26;20(40):12745-9. doi: 10.1002/chem.201403130. Epub 2014 Aug 21.
3
"Click" reactions: a versatile toolbox for the synthesis of peptide-conjugates.
Chem Soc Rev. 2014;43(20):7013-39. doi: 10.1039/c4cs00139g. Epub 2014 Jul 4.
4
Investigating peptide sequence variations for 'double-click' stapled p53 peptides.
Org Biomol Chem. 2014 Jun 28;12(24):4074-7. doi: 10.1039/c4ob00742e.
5
Bioorthogonal chemistry: strategies and recent developments.
Chem Commun (Camb). 2013 Dec 7;49(94):11007-22. doi: 10.1039/c3cc44272a.
6
Imidazole-1-sulfonyl azide-based diazo-transfer reaction for the preparation of azido solid supports for solid-phase synthesis.
ACS Comb Sci. 2013 Jul 8;15(7):331-4. doi: 10.1021/co4000437. Epub 2013 Jun 6.
7
Interfacial energy conversion in Ru(II) polypyridyl-derivatized oligoproline assemblies on TiO2.
J Am Chem Soc. 2013 Apr 10;135(14):5250-3. doi: 10.1021/ja312143h. Epub 2013 Mar 26.
8
Water-soluble and pH-responsive polymeric nanotubes from cyclic peptide templates.
Chemistry. 2013 Feb 4;19(6):1955-61. doi: 10.1002/chem.201203602. Epub 2013 Jan 7.
9
A modular and noncovalent transduction system for leucine-zipper-tagged proteins.
Chembiochem. 2011 Oct 17;12(15):2294-7. doi: 10.1002/cbic.201100481.
10
Noncovalent template-assisted mimicry of multiloop protein surfaces: assembling discontinuous and functional domains.
J Am Chem Soc. 2012 Aug 15;134(32):13208-11. doi: 10.1021/ja305360q. Epub 2012 Aug 6.
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