Rhodopeptins, novel cyclic tetrapeptides with antifungal activities from Rhodococcus sp.. III. Synthetic study of rhodopeptins

Journal of Antibiotics

Volumn 52, Issue 8, 1999, Pages 710-720

  Chiba, Hiroyuki ^a   Agematu, Hitosi ^a   Sakai, Kazuya ^a   Dobashi, Kazuyuki ^a   Yoshioka, Takeo ^a  

^a MERCIAN CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFUNGAL AGENT; RHODOPEPTIN; TETRAPEPTIDE; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ARTICLE; CYCLIZATION; DIASTEREOISOMER; DRUG SYNTHESIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIC MIXTURE; RHODOCOCCUS;

RHODOCOCCUS;

EID: 0032872546     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.7164/antibiotics.52.710     Document Type: Article

References (15)

1. CHIBA, H.; H. AGEMATU, R. KANETO, T. TERASAWA, K. SAKAI, K. DOBASHI & T. YOSHIOKA: Rhodopeptins, novel cyclic tetrapeptides with antifungal activity from Rhodococcus sp. I. Taxonomy, fermentation, isolation, physico-chemical properties, and biological activites. J. Antibiotics 52: 695-699, 1999
2. CHIBA, H.; H. AGEMATU, K. DOBASHI & T. YOSHIOKA: Rhodopeptins, novel cyclic tetrapeptides with antifungal activity from Rhodococcus sp. II. Structure elucidation. J. Antibiotics 52: 700-709, 1999
3. NAKAYAMA, M.; S. SHINKE, Y. MATSUSHITA, S. OHIRA & S. HAYASHI: Allylic oxidation of methyl 2-alkenoates. Bull. Chem. Soc., Jpn. 52: 184-185, 1979
4. FURUKAWA, M.; T. OKAWARA & Y. TERAWAKI: Asymmetric syntheses of β-amino acids by the addition of chiral amines C=C double bonds. Chem. Pharm. Bull. 25: 1319-1325, 1977
5. HAWKINS, J. M. & G. C. FU: Asymmetric Michael reactions of 3,5-dihydro-4H-dinaphth[2,1-c: 1′,2′-e]azepine with methyl crotonate. J. Org. Chem. 51: 2820-2822, 1986
6. DAVIES, S. G. & O. ICHIHARA: Asymmetric synthesis of R-β-amino butanoic acid and S-β-tyrosine: Homochiral lithium amide equivalents for Michael additions to α,β-unsaturated esters. Tetrahedron: Asymmetry 2: 183-186, 1991
7. COLE, D. C.: Recent stereoselective synthetic approaches to β-amino acids. Tetrahedron 50: 9517-9582, 1994, and references therein.
8. DAVIES, S. G. & O. ICHIHARA: Asymmetric synthesis of β-amino acids via the Michael addition of chiral metal amides. Yuki Gosei Kagaku Kyokaishi 55: 42-50, 1997
9. GMEINER, P.: An efficient and practical EPC synthesis of β-amino acids from L-asparagine. Arch. Pharm. (Weinheim) 324: 551-557, 1991
10. GMEINER, P.: General synthesis of enantiomerically pure β-amino acids. Tetrahedron Lett. 31: 5717-5720, 1990
11. BUNNAGE, M. E.; A. J. BURKE, S. G. DAVIES & C. J. GOODWIN: Asymmetric synthesis of N-terminal component of microginin: (2S,3R)-3-Amino-2-hydroxydecanoic acid, its (2R,3R)-epimer and (3R)-3-aminodecanoic acid. Tetrahedron: Asymmetry 6: 165-176, 1995
12. OLSEN, R. K.; S. APPARAO & K. L. BHAT: Synthesis of a model analogue of the cyclic decadepsipeptide intercalating agent luzopeptin A (antibiotic BBM 928A) containing proline, valine, and unsubstituted quinoline substituents. J. Org. Chem. 51: 3079-3085, 1986
13. 29-desmethyl-RA-VII: Identification of the pharmacophore and reversal of the subunit functional roles. J. Am. Chem. Soc. 115: 3420-3430, 1993
14. BRADY, S. F.; R. M. FREIDINGER, W. J. PALEVEDA, C. D. COLTON, C. F. HOMNICK, W. L. WHITTER, P. CURLEY, R. F. NUTT & D. F. VEBER: Large-scale synthesis of a cyclic hexapeptide analogue of somatostatin. J. Org. Chem. 52: 764-769, 1987
15. UEHARA, T.; N. SHIDA & Y. YAMAMOTO: New type of cyclization of α,β,χ,ψ-unsaturated dioic acid esters through tandem conjugate additions by using lithium N-benzyl-N-(trimethylsilyl)amide as a nitrogen nucleophile. J. Org. Chem. 57: 3139-3145, 1992