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Volumn 48, Issue 6, 2007, Pages 979-983

Bacillus subtilis epoxide hydrolase-catalyzed preparation of enantiopure 2-methylpropane-1,2,3-triol monobenzyl ether and its application to expeditious synthesis of (R)-bicalutamide

Author keywords

(R) 1 Benzyloxy 2 methylpropane 2,3 diol; Bicalutamide; Diol; Epoxide hydrolase; Kinetic resolution

Indexed keywords

2 METHYLPROPANE 1,2,3 TRIOL MONOBENZYL ETHER; BENZYL DERIVATIVE; BICALUTAMIDE; EPOXIDE HYDROLASE; UNCLASSIFIED DRUG;

EID: 33846173011     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.12.011     Document Type: Article
Times cited : (32)

References (30)
  • 12
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    • note
    • 20
  • 14
    • 0016635708 scopus 로고    scopus 로고
    • Yamaguchi, H.; Shirasaka, N.; Ikunaka, M. (Nagase & Co., Ltd.), Japan, Kokai Tokkyo Koho 2004-349, 377, 2004; Chem. Abstr. 2006, 145, 59218, also orally presented; Yamaguchi, H.; Shirasaka, N.; Sakoda, A.; Ikunaka, M. Development of a useful biocatalyst (epoxide hydrolase) to prepare optically active 1,2-diols. 2F2-42, the 85th annual meeting of Chemical Society of Japan, March 26-29, Yokohama, 2005. Experimental procedures were as follows: Stock cultures of microorganisms were explored from scratch for those capable of (S)-selective hydrolysis of (±)-7, which led to identification of a wild strain of B. subtilis (JCM 10629) as producing an EH of the required stereoselectivity. The gene encoding epoxide hydrolase (yfhM) was cloned from the genomic DNA of B. subtilis by the standard method. Both amylase promoter and terminator sequences were cloned from the genomic DNA of Bacillus amyloliquefaciens NBRC 15535. The amylase promoter, the epoxide hydrolase gene, and the amylase terminator were inserted into an expression vector pUB110 in this order. The competent cells of B. subtilis MT-2 (deficient in neutral protease) were transformed with the plasmid vector thus constructed and the clone (dubbed Tamy 2 strain) was then selected which exhibited the epoxide hydrolase activity. For the utilization of amylase promoter, see: Saito, N.; Yamamoto, K. J. Bacteriol. 1975, 121, 848-856.
  • 15
    • 33846154811 scopus 로고    scopus 로고
    • note
    • R(min) = 20.1] was detected. Its NMR spectrum was identical with that of racemic sample.
  • 21
    • 33846122151 scopus 로고    scopus 로고
    • note
    • 2)]; HPLC: 100% ee. Caution: when the mixture is kept at a temperature lower than -30 °C for a prolonged period, crystals of (R)-4 would suffer from contamination with (S)-4.
  • 24
    • 33846166962 scopus 로고    scopus 로고
    • note
    • +): 420.1295; found: m/z 420.1290.
  • 26
    • 33846162143 scopus 로고    scopus 로고
    • note
    • +): 312.0019; found: m/z 312.0701.
  • 27
    • 33846141668 scopus 로고    scopus 로고
    • note
    • R(min) = 57.2] was detected.
  • 28
    • 33846127330 scopus 로고    scopus 로고
    • Soros, B.; Tuba, Z.; Galik, G.; Bor, A.; Demeter, A.; Trischler, F.; Harvath, J.; Brlik, J. WO 2001000608, 2002; Chem. Abstr. 2002, 134, 86040.
  • 29
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    • note
    • 10


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.