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

[1] Sugar-assisted glycopeptide ligation [J].

Brik, A ;

Yang, YY ;

Ficht, S ;

Wong, CH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (17) :5626-5627

[2] Native Chemical Ligation at Valine: A Contribution to Peptide and Glycopeptide Synthesis [J].

Chen, Jin ;

Wan, Qian ;

Yuan, Yu ;

Zhu, Jianglong ;

Danishefsky, Samuel J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (44) :8521-8524

[3] Native chemical ligation at phenylalanine [J].

Crich, David ;

Banerjee, Abhisek .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (33) :10064-+

[4] SYNTHESIS OF PROTEINS BY NATIVE CHEMICAL LIGATION [J].

DAWSON, PE ;

MUIR, TW ;

CLARKLEWIS, I ;

KENT, SBH .

SCIENCE, 1994, 266 (5186) :776-779

[5] Traceless chemical ligations from O-acyl serine sites [J].

El Khatib, Mirna ;

Elagawany, Mohamed ;

Jabeen, Farukh ;

Todadze, Ekaterina ;

Bol'shakov, Oleg ;

Oliferenko, Alexander ;

Khelashvili, Levan ;

El-Feky, Said A. ;

Asiri, Abdullah ;

Katritzky, Alan R. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (25) :4836-4838

[6] Second-generation sugar-assisted ligation: A method for the synthesis of cysteine-containing glycopeptides [J].

Ficht, Simon ;

Payne, Richard J. ;

Brik, Ashraf ;

Wong, Chi-Huey .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (31) :5975-5979

[7] Long-Range Intramolecular S → N Acyl Migration: A Study of the Formation of Native Peptide Analogues via 13-, 15-, and 16-Membered Cyclic Transition States [J].

Ha, Khanh ;

Chahar, Mamta ;

Monbaliu, Jean-Christophe M. ;

Todadze, Ekaterina ;

Hansen, Finn K. ;

Oliferenko, Alexander A. ;

Ocampo, Charles E. ;

Leino, David ;

Lillicotch, Aaron ;

Stevens, Christian V. ;

Katritzky, Alan R. .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (06) :2637-2648

[8] Native chemical ligation at valine [J].

Haase, Christian ;

Rohde, Heike ;

Seitz, Oliver .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (36) :6807-6810

[9] The Mercaptomethyl Group Facilitates an Efficient One-Pot Ligation at Xaa-Ser/Thr for (Glyco)peptide Synthesis [J].

Hojo, Hironobu ;

Ozawa, Chinatsu ;

Katayama, Hidekazu ;

Ueki, Akiharu ;

Nakahara, Yuko ;

Nakahara, Yoshiaki .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (31) :5318-5321

[10] Chemical Ligation of S-Scylated Cysteine Peptides to Form Native Peptides via 5-, 11-, and 14-Membered Cyclic Transition States [J].

Katritzky, Alan R. ;

Tala, Srinivasa R. ;

Abo-Dya, Nader E. ;

Ibrahim, Tarek S. ;

El-Feky, Said A. ;

Gyanda, Kapil ;

Pandya, Keyur M. .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (01) :85-96

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