STRUCTURAL ELUCIDATION OF ACULEXIMYCIN .3. PLANAR STRUCTURE OF ACULEXIMYCIN, BELONGING TO A NEW CLASS OF MACROLIDE ANTIBIOTICS

被引:12
作者
MURATA, H
SUZUKI, K
TABAYASHI, T
HATTORI, C
TAKADA, Y
HARADA, K
SUZUKI, M
IKEMOTO, T
SHIBUYA, T
HANEISHI, T
TORIKATA, A
ITEZONO, Y
NAKAYAMA, N
机构
[1] MEIJO UNIV,FAC PHARM,NAGOYA,AICHI 468,JAPAN
[2] TEIKYO UNIV,SCH MED,ITABASHI KU,TOKYO 173,JAPAN
[3] SANKYO CO LTD,FERMENTAT RES LABS,TOKYO 140,JAPAN
[4] NIPPON ROCHE RES CTR,KAMAKURA,KANAGAWA 247,JAPAN
关键词
D O I
10.7164/antibiotics.48.838
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
The planar structure of aculeximycin (1) produced by Streptosporangium albidum has been determined by spectral methods and chemical degradations such as 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU)-methanol reaction, ozonolysis, and periodative oxidation. The antibiotic consists of a 30-membered polyhydroxy lactone ring, an alpha, beta-unsaturated ester group, an intramolecular hemiketal, an oligosaccharide (aculexitriose), a neutral sugar and an amino sugar. The structure of aculeximycin is closely related to those of sporaviridins produced by Streptosporangium viridogriseum. We consider that aculeximycin and sporaviridins belong to a new class of macrolide antibiotics, which is different from the polyol macrolides produced by Streptomyces.
引用
收藏
页码:838 / 849
页数:12
相关论文
共 23 条
[1]   ISOLATION OF NEOCOPIAMYCIN A FROM STREPTOMYCES-HYGROSCOPICUS VAR CRYSTALLOGENES, THE COPIAMYCIN SOURCE [J].
ARAI, T ;
UNO, J ;
HORIMI, I ;
FUKUSHIMA, K .
JOURNAL OF ANTIBIOTICS, 1984, 37 (02) :103-109
[2]   ON THE STRUCTURE ELUCIDATION OF NIPHIMYCIN .1. PURIFICATION AND CHARACTERIZATION OF THE NIPHIMYCIN-I-ALPHA AND NIPHIMYCIN-I-BETA - DEGRADATION BY NITRIC-ACID [J].
BASSI, L ;
JOOS, B ;
GASSMANN, P ;
KAISER, HP ;
LEUENBERGER, H ;
KELLERSCHIERLEIN, W .
HELVETICA CHIMICA ACTA, 1983, 66 (01) :92-117
[3]   STUDIES ON MACROCYCLIC LACTONE ANTIBIOTICS .6. SKELETAL STRUCTURE OF COPIAMYCIN [J].
FUKUSHIMA, K ;
ARAI, T ;
IWASAKI, S ;
NAMIKOSHI, M ;
OKUDA, S .
JOURNAL OF ANTIBIOTICS, 1982, 35 (11) :1480-1494
[4]   METABOLIC PRODUCTS OF MICROORGANISMS .226. STRUCTURAL ELUCIDATION OF NIPHIMYCIN .3. IDENTITY OF SCOPAFUNGIN AND NIPHIMYCIN-I - POSITION OF THE MALONYL RESIDUE OF NIPHIMYCIN AND COPIAMYCIN [J].
GASSMANN, P ;
HAGMANN, L ;
KELLERSCHIERLEIN, W ;
SAMAIN, D .
HELVETICA CHIMICA ACTA, 1984, 67 (03) :696-705
[5]   SECONDARY METABOLITES BY CHEMICAL-SCREENING .2. AMYCIN-A AND AMYCIN-B, 2, NOVEL NIPHIMYCIN ANALOGS ISOLATED FROM A HIGH PRODUCER STRAIN OF ELAIOPHYLIN AND NIGERICIN [J].
GRABLEY, S ;
HAMMANN, P ;
RAETHER, W ;
WINK, J ;
ZEECK, A .
JOURNAL OF ANTIBIOTICS, 1990, 43 (06) :639-647
[6]   ACULEXIMYCIN, A NEW ANTIBIOTIC FROM STREPTOSPORANGIUM-ALBIDUM .1. TAXONOMY OF PRODUCING ORGANISM AND FERMENTATION [J].
IKEMOTO, T ;
MATSUNAGA, H ;
KONISHI, K ;
OKAZAKI, T ;
ENOKITA, R ;
TORIKATA, A .
JOURNAL OF ANTIBIOTICS, 1983, 36 (09) :1093-1096
[7]   ACULEXIMYCIN, A NEW ANTIBIOTIC FROM STREPTOSPORANGIUM-ALBIDUM .2. ISOLATION, PHYSICOCHEMICAL AND BIOLOGICAL PROPERTIES [J].
IKEMOTO, T ;
KATAYAMA, T ;
SHIRAISHI, A ;
HANEISHI, T .
JOURNAL OF ANTIBIOTICS, 1983, 36 (09) :1097-1100
[8]  
IWASAKI S, 1982, CHEM PHARM BULL, V30, P1669
[9]  
IWASAKI S, 1982, CHEM PHARM BULL, V30, P4006
[10]  
KELLERSCHIERLEI.W, 1983, HELV CHIM ACTA, V66, P226