The novel gluconeogenesis inhibitors FR225659 and FR225656 from Helicomyces sp. No. 19353. III. Structure determination

Journal of Antibiotics

Volumn 56, Issue 8, 2003, Pages 694-699

  Zenkoh, Tatsuya ^a   Ohtsu, Yoshihiro ^a   Yoshimura, Seiji ^a   Shigematsu, Nobuharu ^a   Takase, Shigehiro ^a   Hino, Motohiro ^a  

^a ASTELLAS PHARMA INC   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3 CHLORO 4 HYDROXYARGININE; 3 HYDROXY 3 METHYLPROLINE; AMINO ACID DERIVATIVE; ANTIDIABETIC AGENT; DEHYDROISOLEUCINE; DEHYDROVALINE; FR 225656; FR 225659; NEW DRUG; TRIPEPTIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DIABETES MELLITUS; DRUG DEGRADATION; DRUG ISOLATION; DRUG PURIFICATION; DRUG SCREENING; GLUCONEOGENESIS; HELICOMYCES; HYPHOMYCETES; PRIORITY JOURNAL; SPECIES DIFFERENCE; SPECTROSCOPY; STRUCTURE ACTIVITY RELATION;

HELICOMYCES;

EID: 0041469931     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.7164/antibiotics.56.694     Document Type: Article

References (10)

1. Ohtsu, Y.; H. Sasamura, Y. Tsurumi, S. Takase, M. Hashimoto, T. Shibata M. Hino & T. Fujii: The novel gluconeogenesis inhibitors FR225659 and related compounds that originate from Helicomyces sp. No. 19353. I. Taxonomy, fermentation, isolation and physicochemical properties. J. Antibiotics 56: 682-688, 2003
2. Ohtsu, Y.; H. Sasamura, T. Shibata, H. Nakajima, M. Hino & T. Fujii: The novel gluconeogenesis inhibitors FR225659 and related compounds that originate from Helicomyces sp. No. 19353. II. Biological profiles. J. Antibiotics 56: 689-693, 2003
3. This chiral phthalic acid was reported as an useful auxiliary for a purpose of X-ray crystallography. See, Harada, N.; T. Nehira, T. Soutome, N. Hiyoshi & F. Kido: Chiral phthalic acid amide, a chiral auxiliary useful for enantiomer resolution and X-ray crystallographic determination of the absolute stereochemistry of alcohols. Enantiomer 1: 35-39, 1996
4. Rami Reddy, M. V.; M. K. Harper & D. J. Faulkner: Eurypamide A, a cyclic tripeptide from the Palauan sponge Microciona eurypa. Tetrahedron 54: 10649-10656, 1998
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6. For an example of 4-hydroxy-NG-methyl-Arg, see b) Imamura, N.; I. Motoike, M. Noda, K. Adachi, A. Konnno & H. Fukami: Argimicin A, a novel anti-cyanobacterial compound produced by an algae-lysing bacterium. J. Antibiotics 53: 1317-1319, 2000
7. Umezawa, K.; K. Nakazawa, Y. Ikeda, H. Naganawa & S. Kondo: Polyoxypeptins A and B produced by Streptomyces: Apotosis-inducing cyclic depsipeptides containing the novel amino acid (2S,3R)-3-hydroxy-3-methylproline. J. Org. Chem. 64: 3034-3038, 1999
8. Noguchi, Y.; H. Uchiro, T. Yamada & S. Kobayashi: Synthetic study of polyoxypeptin: stereoselective synthesis of (2S,3R)-3-hydroxy-3-methylproline. Tetrahedron Letters 42: 5253-5256, 2001
9. Qin, D.-G.; H.-Y Zha & Z.-J. Yao: Enantioselective synthesis of (2S,3R)-3-hydroxy-3-methylproline, a novel amino acid found in polyoxypeptins. J. Org. Chem. 67: 1038-1040, 2002
10. 2-mediated cyclization. Tetrahedron Letters 43: 4695-4698, 2002