New cyclic depsipeptide antibiotics, clavariopsins A and B, produced by an aquatic hyphomycetes, Clavariopsis aquatica -: 2.: Structure analysis

被引:21
作者
Suzuki, Y
Ojika, M [1 ]
Sakagami, Y
Kaida, K
Fudou, R
Kameyama, T
机构
[1] Nagoya Univ, Grad Sch Bioagr Sci, Chikusa Ku, Nagoya, Aichi 4648601, Japan
[2] Ajinomoto Co Inc, Pharmaceut Res Labs, Kawasaki Ku, Kawasaki, Kanagawa 2108681, Japan
[3] Ajinomoto Co Inc, Cent Res Labs, Kawasaki Ku, Kawasaki, Kanagawa 2108681, Japan
关键词
D O I
10.7164/antibiotics.54.22
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 structures of new cyclic decadepsipeptides, clavariopsins A and B, were determined to be cyclo[-(R)-2-hydroxyisovaleryl-L-pipecolyl-L-MeVal-L-Val-L-MeAsp-L-Melle-L-Melle-Gly-L-MeVal-L-Try(OMe)-] and cyclo[-(R)-2-hydroxyisovaleryl-L-pipecolyl-L-MeIle-L-MeIle-Gly-L-MeVal-L-Tyr(OME)-], respectively, by spectroscopic analysis, especially using 2D NMR techniques. The absolute stereochemistry was elucidated by the advanced MARFEY'S method and chiral HPLC analysis.
引用
收藏
页码:22 / 28
页数:7
相关论文
共 10 条
[1]   DERIVATIVES OF A NOVEL CYCLOPEPTOLIDE .1. SYNTHESIS, ANTIFUNGAL ACTIVITY, AND STRUCTURE-ACTIVITY-RELATIONSHIPS [J].
EMMER, G ;
GRASSBERGER, MA ;
MEINGASSNER, JG ;
SCHULZ, G ;
SCHAUDE, M .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (13) :1908-1917
[2]   A nonempirical method using LC/MS for determination of the absolute configuration of constituent amino acids in a peptide: Combination of Marfey's method with mass spectrometry and its practical application [J].
Fujii, K ;
Ikai, Y ;
Oka, H ;
Suzuki, M ;
Harada, K .
ANALYTICAL CHEMISTRY, 1997, 69 (24) :5146-5151
[3]   A nonempirical method using LC/MS for determination of the absolute configuration of constituent amino acids in a peptide: Elucidation of limitations of Marfey's method and of its separation mechanism [J].
Fujii, K ;
Ikai, Y ;
Mayumi, T ;
Oka, H ;
Suzuki, M ;
Harada, K .
ANALYTICAL CHEMISTRY, 1997, 69 (16) :3346-3352
[4]   A METHOD USING LC/MS FOR DETERMINATION OF ABSOLUTE-CONFIGURATION OF CONSTITUENT AMINO-ACIDS IN PEPTIDE - ADVANCED MARFEYS METHOD [J].
HARADA, K ;
FUJII, K ;
MAYUMI, T ;
HIBINO, Y ;
SUZUKI, M ;
IKAI, Y ;
OKA, H .
TETRAHEDRON LETTERS, 1995, 36 (09) :1515-1518
[5]   STRUCTURE OF AUREOBASIDIN-A [J].
IKAI, K ;
TAKESAKO, K ;
SHIOMI, K ;
MORIGUCHI, M ;
UMEDA, Y ;
YAMAMOTO, J ;
KATO, I ;
NAGANAWA, H .
JOURNAL OF ANTIBIOTICS, 1991, 44 (09) :925-933
[6]   New cyclic depsipeptide antibiotics, clavariopsins A and B, produced by an aquatic hyphomycetes, Clavariopsis aquatica -: 1.: Taxonomy, fermentation, isolation, and biological properties [J].
Kaida, K ;
Fudou, R ;
Kameyama, T ;
Tubaki, K ;
Suzuki, Y ;
Ojika, M ;
Sakagami, Y .
JOURNAL OF ANTIBIOTICS, 2001, 54 (01) :17-21
[7]   SDZ-280-446, A NOVEL SEMISYNTHETIC CYCLOPEPTOLIDE - INVITRO AND INVIVO CIRCUMVENTION OF THE P-GLYCOPROTEIN-MEDIATED TUMOR-CELL MULTIDRUG RESISTANCE [J].
LOOR, F ;
BOESCH, D ;
GAVERIAUX, C ;
JACHEZ, B ;
POURTIERMANZANEDO, A ;
EMMER, G .
BRITISH JOURNAL OF CANCER, 1992, 65 (01) :11-18
[8]   DETERMINATION OF D-AMINO ACIDS .2. USE OF A BIFUNCTIONAL REAGENT, 1,5-DIFLUORO-2,4-DINITROBENZENE [J].
MARFEY, P .
CARLSBERG RESEARCH COMMUNICATIONS, 1984, 49 (06) :591-596
[9]   N-METHYLAMINO ACIDS IN PEPTIDE SYNTHESIS .2. NEW SYNTHESIS OF N-BENZYLOXYCARBONYL,N-METHYLAMINO ACIDS [J].
MCDERMOTT, JR ;
BENOITON, NL .
CANADIAN JOURNAL OF CHEMISTRY, 1973, 51 (12) :1915-1919
[10]   STUDIES ON DIASTEREOISOMERIC ALPHA-AMINO ACIDS AND CORRESPONDING ALPHA-HYDROXY ACIDS .7. INFLUENCE OF BETA-CONFIGURATION ON ENZYMIC SUSCEPTIBILITY [J].
WINITZ, M ;
BLOCHFRANKENTHAL, L ;
IZUMIYA, N ;
BIRNBAUM, SM ;
BAKER, CG ;
GREENSTEIN, JP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (11) :2423-2430