An unprecedented side chain conformation of paclitaxel (Taxol(R)): Crystal structure of 7-mesylpaclitaxel

被引：17

作者：

Gao, Q

Chen, SH

机构：

[1] Bristol-Myers Squibb P., Wallingford, CT 06492-7660

[2] OncoRx Inc., New Haven, CT 06511

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 20期

关键词：

D O I：

10.1016/0040-4039(96)00585-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The single-crystal X-ray diffraction study of 7-Mesylpaclitaxel, a bioactive paclitaxel analog, has revealed a novel paclitaxel side chain conformation which differs from any other known conformations, including the hydrophobic collapse and the apolar conformation, as found in solid state and in solution. This conformation appears to be induced by specific interactions of the side chain with solvent. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：3425 / 3428

页数：4

共 15 条

[1]

CHEN SH, 1995, CHEM PHARM TAXOL ITS, P165

[2] The ''hydrophobic collapse'' conformation of paclitaxel (Taxol(R)) has been observed in a non-aqueous environment: Crystal structure of 10-deacetyl-7-epitaxol [J].

Gao, Q ;

Parker, WL .

TETRAHEDRON, 1996, 52 (07) :2291-2300

[3]

GEORG GI, 1995, TAXOL SCI APPL, P317

[4]

Gomez Paloma L, 1994, Chem Biol, V1, P107

[5] TAXOL AND TAXOTERE - DISCOVERY, CHEMISTRY, AND STRUCTURE-ACTIVITY-RELATIONSHIPS [J].

GUENARD, D ;

GUERITTEVOEGELEIN, F ;

POTIER, P .

ACCOUNTS OF CHEMICAL RESEARCH, 1993, 26 (04) :160-167

[6] STRUCTURE OF A SYNTHETIC TAXOL PRECURSOR - N-TERT-BUTOXYCARBONYL-10-DEACETYL-N-DEBENZOYLTAXOL [J].

GUERITTEVOEGELEIN, F ;

GUENARD, D ;

MANGATAL, L ;

POTIER, P ;

GUILHEM, J ;

CESARIO, M ;

PASCARD, C .

ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1990, 46 :781-784

[7] FIRST TOTAL SYNTHESIS OF TAXOL .1. FUNCTIONALIZATION OF THE B-RING [J].

HOLTON, RA ;

SOMOZA, C ;

KIM, HB ;

LIANG, F ;

BIEDIGER, RJ ;

BOATMAN, PD ;

SHINDO, M ;

SMITH, CC ;

KIM, SC ;

NADIZADEH, H ;

SUZUKI, Y ;

TAO, CL ;

VU, P ;

TANG, SH ;

ZHANG, PS ;

MURTHI, KK ;

GENTILE, LN ;

LIU, JH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (04) :1597-1598

[8]

KINGSTON DGI, 1995, TAXANE ANTICANCER AG, P203

[9] CRYSTAL AND MOLECULAR-STRUCTURE OF PACLITAXEL (TAXOL) [J].

MASTROPAOLO, D ;

CAMERMAN, A ;

LUO, YG ;

BRAYER, GD ;

CAMERMAN, N .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1995, 92 (15) :6920-6924

[10] TOTAL SYNTHESIS OF TAXOL [J].

NICOLAOU, KC ;

YANG, Z ;

LIU, JJ ;

UENO, H ;

NANTERMET, PG ;

GUY, RK ;

CLAIBORNE, CF ;

RENAUD, J ;

COULADOUROS, EA ;

PAULVANNAN, K ;

SORENSEN, EJ .

NATURE, 1994, 367 (6464) :630-634

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