PNEUMOCANDINS FROM ZALERION-ARBORICOLA .3. STRUCTURE ELUCIDATION

被引:43
作者
HENSENS, OD
LIESCH, JM
ZINK, DL
SMITH, JL
WICHMANN, CF
SCHWARTZ, RE
机构
[1] Department of Natural Products Chemistry, Merck Research Laboratories, N.J. 07065-0900, P.O. Box 2000 (RY80Y-345), Rahway
关键词
D O I
10.7164/antibiotics.45.1875
中图分类号
Q81 [生物工程学(生物技术)]; Q93 [微生物学];
学科分类号
071005 ; 0836 ; 090102 ; 100705 ;
摘要
Pneumocandin B0 (6) and six related lipopeptides are antifungal and anti-Pneumocystis carinii agents from mutants of Zalerion arboricola, whose structures were determined mainly on the basis of spectroscopic analysis. They belong, along with pneumocandin A0 (L-671,329) previously isolated from these laboratories,1) to the echinocandin class of antifungal agents. The product from base-catalyzed ring opening involving the hemiaminal position of the dihydroxyornithine residue of B0, has been clearly defined as 6b. Modifications were limited to the 3-hydroxy-4-methylproline, 3,4-dihydroxyhomotyrosine and 4,5-dihydroxyornithine residues of pneumocandin A0.
引用
收藏
页码:1875 / 1885
页数:11
相关论文
共 22 条
[1]   NMR SPECTRA AND CONFORMATIONS OF CYCLIC COMPOUNDS .5. MECHANISM OF CH.CH COUPLING IN HETEROCYCLIC COMPOUNDS [J].
ABRAHAM, RJ ;
PARRY, K ;
THOMAS, WA .
JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1971, (03) :446-&
[2]  
ABRAHAM RJ, 1965, J CHEM SOC CHEM COMM, P431
[3]   PNEUMOCANDINS FROM ZALERION-ARBORICOLA .5. GLUTAMIC ACID-DERIVED AND LEUCINE-DERIVED AMINO-ACIDS IN PNEUMOCANDIN A0(L-671,329) AND DISTINCT ORIGINS OF THE SUBSTITUTED PROLINE RESIDUES IN PNEUMOCANDINS A0 AND B0 [J].
ADEFARATI, AA ;
HENSENS, OD ;
JONES, ETT ;
TKACZ, JS .
JOURNAL OF ANTIBIOTICS, 1992, 45 (12) :1953-1957
[4]   BIOSYNTHESIS OF L-671,329, AN ECHINOCANDIN-TYPE ANTIBIOTIC PRODUCED BY ZALERION-ARBORICOLA - ORIGINS OF SOME OF THE UNUSUAL AMINO-ACIDS AND THE DIMETHYLMYRISTIC ACID SIDE-CHAIN [J].
ADEFARATI, AA ;
GIACOBBE, RA ;
HENSENS, OD ;
TKACZ, JS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (09) :3542-3545
[5]   PROTON MAGNETIC RESONANCE SPECTRA CONFIGURATION AND CONFORMATION OF 4-SUBSTITUTED PROLINES [J].
ANDREATTA, RH ;
NAIR, V ;
ROBERTSO.AV .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1967, 20 (12) :2701-+
[6]   H-1 AND C-13 ASSIGNMENTS FROM SENSITIVITY-ENHANCED DETECTION OF HETERONUCLEAR MULTIPLE-BOND CONNECTIVITY BY 2D MULTIPLE QUANTUM NMR [J].
BAX, A ;
SUMMERS, MF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (08) :2093-2094
[7]   SENSITIVITY-ENHANCED TWO-DIMENSIONAL HETERONUCLEAR SHIFT CORRELATION NMR-SPECTROSCOPY [J].
BAX, A ;
SUBRAMANIAN, S .
JOURNAL OF MAGNETIC RESONANCE, 1986, 67 (03) :565-569
[8]   AN IMPROVED METHOD FOR HETERONUCLEAR CHEMICAL-SHIFT CORRELATION BY TWO-DIMENSIONAL NMR [J].
BAX, A ;
MORRIS, GA .
JOURNAL OF MAGNETIC RESONANCE, 1981, 42 (03) :501-505
[9]   OPTIMIZATION OF 2-DIMENSIONAL HOMONUCLEAR RELAYED COHERENCE TRANSFER NMR-SPECTROSCOPY [J].
BAX, A ;
DROBNY, G .
JOURNAL OF MAGNETIC RESONANCE, 1985, 61 (02) :306-320
[10]   CORRELATION OF PROTON CHEMICAL-SHIFTS BY TWO-DIMENSIONAL FOURIER-TRANSFORM NMR [J].
BAX, A ;
FREEMAN, R ;
MORRIS, G .
JOURNAL OF MAGNETIC RESONANCE, 1981, 42 (01) :164-168