Chemical ligation from O-acyl isopeptides via 8-and 11-membered cyclic transition states

被引：4

作者：

Panda, Siva S. ^{[1
]}

Elagawany, Mohamed ^{[1
,2
]}

Marwani, Hadi M. ^{[3
]}

Caliskan, Eray ^{[1
]}

El Khatib, Mirna ^{[1
]}

Oliferenko, Alexander ^{[1
]}

Alamry, Khalid A. ^{[3
]}

Katritzky, Alan R. ^{[1
,3
]}

机构：

[1] Univ Florida, Dept Chem, Ctr Heterocycl Cpds, Gainesville, FL 32611 USA

[2] Misr Univ Sci & Technol, Coll Pharm, Dept Organ Chem, Al Motamayez Dist, Egypt

[3] King Abdulaziz Univ, Dept Chem, Jeddah 21589, Saudi Arabia

来源：

ARKIVOC | 2014年

关键词：

Ligation; serine; threonine; peptide; benzotriazole; NATIVE PEPTIDES; PHASE SYNTHESIS; STRATEGIES; BETA;

D O I：

10.3998/ark.5550190.p008.632

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Unprotected O-acylated serine and O-acylated threonine isopeptides have been synthesized, and their conversion to native tripeptides and tetrapeptides by O- to N-terminus transfer investigated. Ligations involving 8- and 11-membered cyclic transition states are shown experimentally and computationally to be more favorable than intermolecular cross-ligations.

引用

页码：91 / 106

页数：16

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