Chalcomycin: Single-crystal X-ray crystallographic analysis; Biosynthetic and stereochemical correlations with other polyoxo macrolide antibiotics.

被引：15

作者：

Woo, PWK

Rubin, JR

机构：

[1] Parke-Davis Pharmaceutical Res. D., Ann Arbor, MI 48105

来源：

TETRAHEDRON | 1996年 / 52卷 / 11期

关键词：

D O I：

10.1016/S0040-4020(96)00052-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereochemistry of chalcomycin (1), a neutral 16-membered macrolide antibiotic, was established by X-ray crystallography. A correlation model for 16-membered macrolides (2), together with its biochemical rationale, is presented and applied to the configurational assignment of seven other analogous neutral macrolides (aldgamycins F, G, CP-61,884 complex, neutramycin, and swalpamycin). The chalcomycin molecule appears to be conformationally restrained in a rigid manner.

引用

页码：3857 / 3872

页数：16

共 42 条

[1] BUTTE JC, 1962, FED PROC, V21, P89
[2] MACROLIDE BIOSYNTHESIS .4. INTACT INCORPORATION OF A CHAIN-ELONGATION INTERMEDIATE INTO ERYTHROMYCIN
CANE, DE
YANG, CC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (04) : 1255 - 1257
[3] MACROLIDE BIOSYNTHESIS .3. STEREOCHEMISTRY OF THE CHAIN-ELONGATION STEPS OF ERYTHROMYCIN BIOSYNTHESIS
CANE, DE
LIANG, TC
TAYLOR, PB
CHANG, C
YANG, CC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (16) : 4957 - 4964
[4] POLYKETIDE BIOSYNTHESIS - MOLECULAR RECOGNITION OR GENETIC PROGRAMMING
CANE, DE
[J]. SCIENCE, 1994, 263 (5145) : 338 - 340
[5] UNIFIED STEREOCHEMICAL MODEL OF POLYETHER ANTIBIOTIC-STRUCTURE AND BIOGENESIS
CANE, DE
CELMER, WD
WESTLEY, JW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (11) : 3594 - 3600
[6] MACROLIDE BIOSYNTHESIS .7. INCORPORATION OF POLYKETIDE CHAIN ELONGATION INTERMEDIATES INTO METHYMYCIN
CANE, DE
LAMBALOT, RH
PRABHAKARAN, PC
OTT, WR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (02) : 522 - 526
[7] CELMER W D, 1971, Pure and Applied Chemistry, V28, P413, DOI 10.1351/pac197128040413
[8] SWALPAMYCIN, A NEW MACROLIDE ANTIBIOTIC .2. STRUCTURE ELUCIDATION
CHATTERJEE, S
REDDY, GCS
FRANCO, CMM
RUPP, RH
GANGULI, BN
FEHLHABER, HW
KOGLER, H
[J]. JOURNAL OF ANTIBIOTICS, 1987, 40 (10) : 1368 - 1374
[9] THE STRUCTURE OF ACUMYCIN - A 16-MEMBERED RING MACROLIDE ANTIBIOTIC
CLARDY, J
FINERMOORE, J
WEILER, L
WILEY, DC
[J]. TETRAHEDRON, 1981, 37 : 91 - 97
[10] ACCUMULATION OF 6-DEOXYERYTHRONOLIDE-B IN A NORMAL STRAIN OF STREPTOMYCES-ERYTHREUS AND HYDROXYLATION AT CARBON-6 OF THE ERYTHRANOLIDE RING-SYSTEM BY A SOLUBLE NON-INDUCED CELL-FREE ENZYME-SYSTEM
CORCORAN, JW
VYGANTAS, AM
[J]. BIOCHEMISTRY, 1982, 21 (02) : 263 - 269

← 1 2 3 4 5 →