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Volumn 52, Issue 11, 1996, Pages 3857-3872

Chalcomycin: Single-crystal X-ray crystallographic analysis; biosynthetic and stereochemical correlations with other polyoxo macrolide antibiotics

Author keywords

[No Author keywords available]

Indexed keywords

ACUMYCIN; CHALCOMYCIN; KITASAMYCIN DERIVATIVE; MACROLIDE; MARIDOMYCIN III; MYCINAMICIN DERIVATIVE; MYCINOLIDE IV; NEUTRAMYCIN; ROSARAMICIN; UNCLASSIFIED DRUG;

EID: 0030009686     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)00052-X     Document Type: Article
Times cited : (15)

References (49)
  • 8
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    • (e) Cane, D. E. Science 1994, 263, 338-340.
    • (1994) Science , vol.263 , pp. 338-340
    • Cane, D.E.1
  • 11
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    • Gottlieb, D.; Shaw, P.D., Eds.; Springer-Verlag
    • Jordan, D. C. In Antibiotics, I; Gottlieb, D.; Shaw, P.D., Eds.; Springer-Verlag: 1967; p. 446-450.
    • (1967) Antibiotics , vol.1 , pp. 446-450
    • Jordan, D.C.1
  • 35
    • 85029980992 scopus 로고    scopus 로고
    • note
    • (c) In structure, model A (21, Fig. 4) is identical to Celmer's model for 14-membered macrolides; in function, model A "serves all the known 12-and 14-membered ring macrolides and includes chiral centers at C-3, C-5, C-6, and C-8 in 16-membered ring macrolides" (page 3595, reference 20b).
  • 36
    • 0020043971 scopus 로고
    • (a) It has been demonstrated that C6 hydroxylation of 6-dEB (23) occurred with configuration retention, late in the biosynthetic pathway (Corcoran, J. W.; Vygantas, A. M. Biochemistry 1982, 21, 263).
    • (1982) Biochemistry , vol.21 , pp. 263
    • Corcoran, J.W.1    Vygantas, A.M.2
  • 37
    • 85029973272 scopus 로고    scopus 로고
    • note
    • (b) Similarly, for the stereochemical models 2, 21 and 22, any "extra" hydroxyl group at a given chiral center are considered introduced with retention of configuration at a late stage (after cycle 6 in Fig. 5b).
  • 40
    • 85029979904 scopus 로고    scopus 로고
    • note
    • 1b and is analogous to the epoxide structure of the 14-membered oleandomycin (24; Fig. 4). (b) The established chirality at C8 of chalcomycin allows assignment to the corresponding center in the other neutral 16-membered macrolides (15,17, Fig. 3) with certainty.
  • 41
    • 85029993847 scopus 로고    scopus 로고
    • note
    • 2e
  • 46
    • 0016423878 scopus 로고
    • (a) Some crystallographic properties of chalcomycin, reported previously (Krc. J., Jr.; Scott, R. B. Microscope 1975, 23, 15; C.A. 1975, 83. 51293u), were particularly useful in determining the molecular weight of the compound, (b) A previous attempted single-crystal X-ray crystallographic analysis of chalcomycin as its heavy atom derivative was unsuccessful. The derivative, bis-bromoacetyl chalcomycin (crystals from methanol, mp 114-119 °C) lost its crystallinity under the X-ray beam (George A. Sim, unpublished results, 1966).
    • (1975) Microscope , vol.23 , pp. 15
    • Krc J., Jr.1    Scott, R.B.2
  • 47
    • 85029986615 scopus 로고
    • (a) Some crystallographic properties of chalcomycin, reported previously (Krc. J., Jr.; Scott, R. B. Microscope 1975, 23, 15; C.A. 1975, 83. 51293u), were particularly useful in determining the molecular weight of the compound, (b) A previous attempted single-crystal X-ray crystallographic analysis of chalcomycin as its heavy atom derivative was unsuccessful. The derivative, bis-bromoacetyl chalcomycin (crystals from methanol, mp 114-119 °C) lost its crystallinity under the X-ray beam (George A. Sim, unpublished results, 1966).
    • (1975) C.A. , vol.83
  • 48
    • 0042483221 scopus 로고
    • unpublished results
    • (a) Some crystallographic properties of chalcomycin, reported previously (Krc. J., Jr.; Scott, R. B. Microscope 1975, 23, 15; C.A. 1975, 83. 51293u), were particularly useful in determining the molecular weight of the compound, (b) A previous attempted single-crystal X-ray crystallographic analysis of chalcomycin as its heavy atom derivative was unsuccessful. The derivative, bis-bromoacetyl chalcomycin (crystals from methanol, mp 114-119 °C) lost its crystallinity under the X-ray beam (George A. Sim, unpublished results, 1966).
    • (1966)
    • Sim, G.A.1
  • 49
    • 85029991453 scopus 로고    scopus 로고
    • Deposited at the Cambridge Crystallographic Data Centre
    • Deposited at the Cambridge Crystallographic Data Centre.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.