MICROBIOLOGIC OXIDATION OF ESTRATRIENES AND ESTRATETRAENES BY STREPTOMYCES-ROSEOCHROMOGENES ATCC-13400

被引:8
作者
FERRER, JC [1 ]
CALZADA, V [1 ]
BONET, JJ [1 ]
机构
[1] CETS INST QUIM SARRIA,DEPT ORGAN CHEM,E-08017 BARCELONA,SPAIN
关键词
STEROIDS; ESTRATRIENES; ESTRATETRAENES; C-13; NMR; STREPTOMYCES-ROSEOCHROMOGENES ATCC-13400; MICROBIOLOGIC OXIDATION;
D O I
10.1016/0039-128X(90)90096-T
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Incubation of estrone (1a) with Streptomyces roseochromogenes ATCC 13400 yielded a mixture of 3,16-alpha-dihydroxyestra-1,3,5(10)-trien-17-one (3a) and 3, 17-beta-dihydroxyestra-1,3,5(10)-trien-16-one (4a). Transformation of 3-methoxyestra-1,2,5(10)-trien-17-one (1b), 3-hydroxyestra-1,35(10),9(11)-tetraen-17-one (2a), and 3-methoxyestra-1,3,5(10),9(11)-tetraen-17-one (2b) with the same microorganism gave the corresponding mixtures of 16-alpha-hydroxy-17-ketones and 17-beta-hydroxy-16-ketones (3b and 4b, 6a and 7a, 6b and 7b, respectively). In addition, these three last experiments, the 16-beta-17-beta-dihydroxy derivatives 5b, 8a, and 8b, respectively, were also isolated. The complete assignments of the C-13 nuclear magnetic resonance spectra of these compounds are given.
引用
收藏
页码:390 / 394
页数:5
相关论文
共 20 条
[1]  
Charney, Herzog, Microbial Transformation of Steroids, (1967)
[2]  
Williamson, Van Orden, Rosazza, Microbiological hydroxylation of estradiol: formation of 2- and 4-hydroxy-estradiol by Aspergillus alliaceus, Appl Environ Microbiol, 49, pp. 563-567, (1985)
[3]  
Schubert, Le Dinh, Kaufmann, Hoerhold, Microbial hydroxylations of estratrienes, Acta Biol Med Ger, 34, pp. 173-180, (1975)
[4]  
Laskin, Grabowich, Junta, Meyers, Fried, Microbial hydroxylation of estrone and estradiol in the 6β,70α, and 15α positions, J Org Chem, 29, pp. 1333-1336, (1964)
[5]  
Crabbe, Casas-Campillo, Steroids CCLXI Microbiological hydroxylation ofestrane derivatives with Fusariummoniliforme (Gibberella fujikuroi), The Journal of Organic Chemistry, 29, pp. 2731-2734, (1964)
[6]  
Maugras, Savigny, Lematre, Microbiological transformation of estrogens. 11/3-Hydroxylation of estradiol in Neurospora crasa, C R Acad Sei Ser D, 276, pp. 3221-3223, (1973)
[7]  
lida, Shinozuka, lizuka, Microbial introduction of a 16α-hydroxyl function into the steroid nucleus, Zeitschrift für allgemeine Mikrobiologie, 19, pp. 557-561, (1979)
[8]  
Iida, lizuka, Introduction of a 16α-hydroxyl function into estrone by Streptomyces roseochromogenes, Zeitschrift AUg Mikrobiol, 17, pp. 507-512, (1977)
[9]  
Levitz, Synthesis of 17β-estradiol-16-C<sup>14</sup>, J Am Chem Soc, 75, pp. 5352-5355, (1953)
[10]  
Collins, Sjovall, The structure and function of estrogens. IV. Synthesis of 17α-ethynylestradiol specifically polydeuterated in ring C, Aust J Chem, 36, pp. 339-360, (1983)