Ligations from Tyrosine Isopeptides via 12-to 19-Membered Cyclic Transition States

被引：14

作者：

Popov, Vadim ^{[1
]}

Panda, Siva S. ^{[1
]}

Katritzky, Alan R. ^{[1
,2
]}

机构：

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

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 15期

关键词：

NATIVE CHEMICAL LIGATION; STAUDINGER LIGATION; GLYCOPEPTIDE LIGATION; ACYL MIGRATION; PEPTIDE; PROTEINS; AUXILIARY; VALINE; AZIDE; FORM;

D O I：

10.1021/jo4009468

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Efficient syntheses of O-acyl Tyr-peptides allow chemical long-range ligation (O-acyl to N-acyl transfer) via each of 12- to 19-membered cyclic transition states. The results represent the first examples of successful isopeptide ligations starting from O-acyl Tyr-peptides.

引用

页码：7455 / 7461

页数：7

共 26 条

[21] Conversion of aryl azides to O-alkyl Imidates via modified staudinger ligation [J].

Restituyo, JA ;

Comstock, LR ;

Petersen, SG ;

Stringfellow, T ;

Rajski, SR .

ORGANIC LETTERS, 2003, 5 (23) :4357-4360

[22] A "traceless" Staudinger ligation for the chemoselective synthesis of amide bonds [J].

Saxon, E ;

Armstrong, JI ;

Bertozzi, CR .

ORGANIC LETTERS, 2000, 2 (14) :2141-2143

[23] Novel and efficient synthesis of difficult sequence-containing peptides through O-N intramolecular acyl migration reaction of O-acyl E isopeptides [J].

Sohma, Y ;

Sasaki, M ;

Hayashi, Y ;

Kimura, T ;

Kiso, Y .

CHEMICAL COMMUNICATIONS, 2004, (01) :124-125

[24] Development of O-acyl isopeptide method [J].

Sohma, Youhei ;

Yoshiya, Taku ;

Taniguchi, Atsuhiko ;

Kimura, Tooru ;

Hayashi, Yoshio ;

Kiso, Yoshiaki .

BIOPOLYMERS, 2007, 88 (02) :253-262

[25]

WIELAND T, 1953, LIEBIGS ANN CHEM, V583, P129

[26] Synthesis of peptides and proteins without cysteine residues by native chemical ligation combined with desulfurization [J].

Yan, LZ ;

Dawson, PE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (04) :526-533

← 1 2 3 →