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Volumn 37, Issue 9, 1998, Pages 1253-1255

Maracin and maracen: New types of ethynyl vinyl ether and α-chloro divinyl ether antibiotics from Sorangium cellulosum with specific activity against mycobacteria

Author keywords

Antibiotics; Myxobacteria; Natural products; Structure elucidation; Vinyl ethers

Indexed keywords

ACETIC ACID; ALPHA CHLORO DIVINYL ETHER; ANTIBACTERIAL ACTIVITY; ANTIBIOTIC SYNTHESIS; ETHYNYL VINYL ETHER; MARACEN; MARACIN; MYCOBACTERIUM TUBERCULOSIS;

EID: 0345367997     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980518)37:9<1253::AID-ANIE1253>3.0.CO;2-T     Document Type: Article
Times cited : (18)

References (22)
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    • (Ed.: J. Lederberg), Academic Press, New York
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    • Gillis, T.P.1    Hastings, R.C.2
  • 6
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    • note
    • The trivial names maracin and maracen were derived from Massai Mara (Kenya), the place where the strain So ce880 was discovered.
  • 7
    • 0344798076 scopus 로고    scopus 로고
    • note
    • In addition to the main components, the following side products were isolated: So ce880: maracin B (95 mg, 19,20-dihydro derivative of 1), maracin C (15 mg, (17Z) isomer of 1), maracin D (20 mg, (17Z) isomer of maracin B), maracin E (3 mg, (4Z) isomer of maracin B); So ce1128: maracen B (186 mg, 19,20-dihydro derivative of 2), maracen C (66 mg, (17Z) isomer of 2), maracen D (62 mg, (17Z) isomer of maracen B).
  • 8
    • 0344798075 scopus 로고    scopus 로고
    • note
    • [6].
  • 9
    • 0344366273 scopus 로고    scopus 로고
    • Compare with the value of 216.5 Hz in ethoxyacetylene: see ref. [8c], p. 151
    • a) Compare with the value of 216.5 Hz in ethoxyacetylene: see ref. [8c], p. 151;
  • 10
    • 0345661009 scopus 로고    scopus 로고
    • (7Z)-2: δ(8-H) = 5.23 (calc.: ref. [8c], p. 118), 5.14 (det.); (7E)-2: δ(8-H) = 4.88 (calc.; ref. [8c], p. 118), 5.02 (det.);
    • b) (7Z)-2: δ(8-H) = 5.23 (calc.: ref. [8c], p. 118), 5.14 (det.); (7E)-2: δ(8-H) = 4.88 (calc.; ref. [8c], p. 118), 5.02 (det.);
  • 12
    • 0345661006 scopus 로고    scopus 로고
    • note
    • Reaction of 1 with LiCl (excess) in acetic acid for 3 h at room temperature gave a mixture of (7E)-2 and (7Z)-2 with a yield of 35%.
  • 13
    • 0004271105 scopus 로고
    • (Ed.: S. Patai), Wiley, New York, reaction of 2 with lithium diisopropylamide in THF for 30 min at 0°C gave 1 with 20% yield
    • Compare P. J. Stang, V. V. Zhdankin in Supplement C2: The Chemistry of Triple-bonded Functional Groups (Ed.: S. Patai), Wiley, New York, 1994, p. 1146-1147; reaction of 2 with lithium diisopropylamide in THF for 30 min at 0°C gave 1 with 20% yield.
    • (1994) Supplement C2: The Chemistry of Triple-bonded Functional Groups , pp. 1146-1147
    • Compare, P.1    Stang, J.2    Zhdankin, V.V.3
  • 14
    • 0344798074 scopus 로고    scopus 로고
    • note
    • -: 317.1753).
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    • T. Galliard, D. R. Phillips, Biochem. J. 1972, 129, 743-753; L. Crombie, D. O. Morgan, E. H. Smith, J. Chem. Soc. Perkin Trans. 1 1991, 567-575; Z.-D. Jiang, W. H. Gerwick, Lipids 1997, 32, 231-235.
    • (1972) Biochem. J. , vol.129 , pp. 743-753
    • Galliard, T.1    Phillips, D.R.2
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    • T. Galliard, D. R. Phillips, Biochem. J. 1972, 129, 743-753; L. Crombie, D. O. Morgan, E. H. Smith, J. Chem. Soc. Perkin Trans. 1 1991, 567-575; Z.-D. Jiang, W. H. Gerwick, Lipids 1997, 32, 231-235.
    • (1997) Lipids , vol.32 , pp. 231-235
    • Jiang, Z.-D.1    Gerwick, W.H.2
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    • C. Xu, X. Sun, J. Yang, D. Yu, Q. Li, Y. Zhang, S. Dou, Yaoxue Xuebao 1986, 21, 772 [Chem. Abstr. 1986, 106, 135232e].
    • (1986) Chem. Abstr. , vol.106
  • 22
    • 0345661001 scopus 로고    scopus 로고
    • note
    • -1.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.