Synthesis of novel proline-thiazole based-cyclic hexa- and octapeptides

被引：17

作者：

Jayaprakash, S ^{[1
]}

Pattenden, G ^{[1
]}

Viljoen, MS ^{[1
]}

Wilson, C ^{[1
]}

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

来源：

TETRAHEDRON | 2003年 / 59卷 / 34期

关键词：

cyclopeptides; amino acid; thiazole;

D O I：

10.1016/S0040-4020(03)00992-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel proline-thiazole based cyclopeptides were produced by cyclooligomerisation of an L-proline thiazole amino acid HCl in the presence of pentafluorophenyl diphenylphosphinate (FDPP) or diphenyl phosphorazidate (DPPA). (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：6637 / 6646

页数：10

共 27 条

[1]

Bertram A, 2000, SYNLETT, P1519

[2]

Bertram A, 2001, SYNLETT, P1873

[3]

Bertram A, 1999, SYNLETT, P1723

[4] Thioamide synthesis: Thioacyl-N-phthalimides as thioacylating agents [J].

Brain, CT ;

Hallett, A ;

Ko, SY .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (12) :3808-3809

[5] THE CHIRAL SYNTHESIS OF THIAZOLE AMINO-ACID ENANTIOMERS [J].

BREDENKAMP, MW ;

HOLZAPFEL, CW ;

VANZYL, WJ .

SYNTHETIC COMMUNICATIONS, 1990, 20 (15) :2235-2249

[6] NEW CYCLIC-PEPTIDES WITH CYTO-TOXIC ACTIVITY FROM THE ASCIDIAN LISSOCLINUM-PATELLA [J].

DEGNAN, BM ;

HAWKINS, CJ ;

LAVIN, MF ;

MCCAFFREY, EJ ;

PARRY, DL ;

VANDENBRENK, AL ;

WATTERS, DJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (06) :1349-1354

[7] Kinetic control of proline amide rotamers:: Total synthesis of trans,trans- and cis,cis-ceratospongamide [J].

Deng, SJ ;

Taunton, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (06) :916-917

[8] Total synthesis of bistratamide D [J].

Downing, SV ;

Aguilar, E ;

Meyers, AI .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (03) :826-831

[9] STRUCTURE-ACTIVITY-RELATIONSHIPS OF THE LISSOCLINAMIDES - CYTOTOXIC CYCLIC-PEPTIDES FROM THE ASCIDIAN LISSOCLINUM-PATELLA [J].

HAWKINS, CJ ;

LAVIN, MF ;

MARSHALL, KA ;

VANDENBRENK, AL ;

WATTERS, DJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (06) :1634-1638

[10] Metal binding of Lissoclinum patella metabolites.: Part 1:: Patellamides A, C and ulithiacyclamide A [J].

Morris, LA ;

Jaspars, M ;

Kettenes-van den Bosch, JJ ;

Versluis, K ;

Heck, AJR ;

Kelly, SM ;

Price, NC .

TETRAHEDRON, 2001, 57 (15) :3185-3197

← 1 2 3 →