Absolute configuration of the fungal metabolite spirolaxine

被引:23
作者
Bava, A
Clericuzio, M
Giannini, G
Malpezzi, L
Meille, SV
Nasini, G
机构
[1] CNR, ICRM, Dipartimento Chim Mat & Ingn Chim Politecn, I-20131 Milan, Italy
[2] Univ Turin, Dipartimento Chim Gen & Organ Applicata, I-10125 Turin, Italy
[3] Sigma Tau Pharmaceut Co, Res & Dev, I-00040 Pomezia, Italy
关键词
basidiomycetes; secondary metabolite; absolute configuration; circular dichroism; angiogenesis; spiro compounds;
D O I
10.1002/ejoc.200400902
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The relative stereochemistry of the four stereocentres of spirolaxine 1, a bioactive 6,5-spiroacetal phthalide secondary metabolite, was determined through single-crystal X-ray analysis. Its absolute configuration was determined by circular dichroism; the experimental spectrum of spirolaxine is in good agreement with that evaluated by means of DeVoe coupled-oscillator calculations. (c) Wiley-VCH Verlag GmbH & Co.
引用
收藏
页码:2292 / 2296
页数:5
相关论文
共 21 条
[1]   SIR97:: a new tool for crystal structure determination and refinement [J].
Altomare, A ;
Burla, MC ;
Camalli, M ;
Cascarano, GL ;
Giacovazzo, C ;
Guagliardi, A ;
Moliterni, AGG ;
Polidori, G ;
Spagna, R .
JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1999, 32 :115-119
[2]   SECONDARY MOLD METABOLITES .27. PHANEROSPORIC ACID, A BETA-RESORCYLATE OBTAINED FROM PHANEROCHAETE-CHRYSOSPORIUM [J].
ARNONE, A ;
ASSANTE, G ;
NASINI, G ;
DEPAVA, OV .
PHYTOCHEMISTRY, 1989, 28 (10) :2803-2806
[3]   SECONDARY MOLD METABOLITES .28. SPIROLAXINE AND SPOROTRICALE - 2 LONG-CHAIN PHTHALIDES PRODUCED BY SPOROTRICHUM-LAXUM [J].
ARNONE, A ;
ASSANTE, G ;
NASINI, G ;
DEPAVA, OV .
PHYTOCHEMISTRY, 1990, 29 (02) :613-616
[4]   HELICOBACTER-PYLORI - ITS ROLE IN DISEASE [J].
BLASER, MJ .
CLINICAL INFECTIOUS DISEASES, 1992, 15 (03) :386-393
[5]  
CANDIANI G, 2002, 23 IUPAC INT S NAT P
[6]  
CATALAN J, 1976, B SOC CHIM BELG, V85, P1013
[7]   ABOUT THE ORIGIN OF THE CHIROPTICAL PROPERTIES OF THE PLANAR DIENE CHROMOPHORE IN CYCLOHEXYLIDENEPROPENE DERIVATIVES [J].
CLERICUZIO, M ;
ROSINI, C ;
PERSICO, M ;
SALVADORI, P .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (14) :4343-4346
[8]  
Clericuzio M, 1999, EUR J ORG CHEM, V1999, P2059
[9]   GENERAL DEFINITION OF RING PUCKERING COORDINATES [J].
CREMER, D ;
POPLE, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (06) :1354-1358
[10]   CJ-12,954 and its congeners, new anti-Helicobacter pylori compounds produced by Phanerochaete velutina: Fermentation, isolation, structural elucidation and biological activities [J].
Dekker, KA ;
Inagaki, T ;
Gootz, TD ;
Kaneda, K ;
Nomura, E ;
Sakakibara, T ;
Sakemi, S ;
Sugie, Y ;
Yamauchi, Y ;
Yoshikawa, N ;
Kojima, N .
JOURNAL OF ANTIBIOTICS, 1997, 50 (10) :833-839