Methyl 2-((succinimidooxy)carbonyl)benzoate (MSB):: A new, efficient reagent for N-phthaloylation of amino acid and peptide derivatives

被引：34

作者：

Casimir, JR ^{[1
]}

Guichard, G ^{[1
]}

Briand, JP ^{[1
]}

机构：

[1] IBMC, Lab Immunol & Chim Therapeut, UPR 9021, CNRS, F-67084 Strasbourg, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 11期

关键词：

D O I：

10.1021/jo016347h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new, efficient, and readily available reagent, methyl 2-((succinimidooxy)carbonyl)benzoate (MSB), for N-phthaloylation of amino acids and amino acid derivatives is described. The phthaloylation procedure is simple and racemization-free and gives excellent results with a-amino acids, a-amino alcohols, dipeptides, alpha-amino carboxamides, and alpha-amino esters.

引用

页码：3764 / 3768

页数：5

共 38 条

[1]

ADRIAENS P, 1978, RECL TRAV CHIM PAY B, V97, P260

[2]

Aguilar N, 1998, SYNTHESIS-STUTTGART, P313

[3] A NOVEL RING CLOSURE IN MICHAELIS-ARBUZOV REACTION OF TRIALKYL PHOSPHITES WITH PHTHALOYL CHLORIDE [J].

BERLIN, KD ;

BURPO, DH ;

PAGILAGA.RU ;

BUDE, D .

CHEMICAL COMMUNICATIONS, 1967, (20) :1060-&

[4] AMINO ACIDS .5. PHTHALYL DERIVATIVES [J].

BILLMAN, JH ;

HARTING, WF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1948, 70 (04) :1473-1474

[5]

BODANSZKY M, 1993, PRACTICE PEPTIDE SYN

[6] A PROCEDURE FOR PHTHALOYLATION UNDER MILD CONDITIONS [J].

BOSE, AK ;

GREER, F ;

PRICE, CC .

JOURNAL OF ORGANIC CHEMISTRY, 1958, 23 (09) :1335-1338

[7] Efficient synthesis of (S)-4-phthalimido-1,3,4,5-tetrahydro-8-(2,6-dichlorobenzyloxy)-3-oxo-2H-2-benzazepin-2-acetic acid (Pht-Hba(2,6-Cl2-Bn)-Gly-OH) [J].

Casimir, JR ;

Tourwé, D ;

Iterbeke, K ;

Guichard, G ;

Briand, JP .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (20) :6487-6492

[8] Conformational restriction of the Tyr53 side-chain in the decapeptide HEL[52-61]:: effects on binding to MHC-II I-Ak molecule and TCR recognition [J].

Casimir, JR ;

Iterbeke, K ;

Van den Nest, W ;

Trescol-Biémont, MC ;

Dumortier, H ;

Muller, S ;

Gerlier, D ;

Rabourdin-Combe, C ;

Tourwé, D ;

Paris, J .

JOURNAL OF PEPTIDE RESEARCH, 2000, 56 (06) :398-408

[9]

Casimir JR, 2001, SYNTHESIS-STUTTGART, P1985

[10]

Casimir JR, 2001, SYNTHESIS-STUTTGART, P75

← 1 2 3 4 →