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Volumn 9, Issue 3, 2007, Pages 521-524

Bacterial preparation of enantiopure unactivated aziridine-2-carboxamides and their transformation into enantiopure nonnatural amino acids and vic-diamines

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; AZIRIDINE; AZIRIDINE 2 CARBOXAMIDE; AZIRIDINE DERIVATIVE; AZIRIDINE-2-CARBOXAMIDE; BENZYL DERIVATIVE; BIOLOGICAL PRODUCT; DIAMINE; DRUG DERIVATIVE; SERINE; UNCLASSIFIED DRUG;

EID: 33847034113     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062895b     Document Type: Article
Times cited : (34)

References (47)
  • 3
    • 0345975526 scopus 로고    scopus 로고
    • For recent reviews, see: a
    • For recent reviews, see: (a) Stamm, H. J. Prakt. Chem. 1999, 341, 319-331.
    • (1999) J. Prakt. Chem , vol.341 , pp. 319-331
    • Stamm, H.1
  • 7
    • 1542375289 scopus 로고    scopus 로고
    • (e) Hu, X. E. Tetrahedron 2004, 60, 2701-2743.
    • (2004) Tetrahedron , vol.60 , pp. 2701-2743
    • Hu, X.E.1
  • 21
    • 33847010606 scopus 로고    scopus 로고
    • Formerly known as Rhodococcus butanica ATCC 21197.
    • Formerly known as Rhodococcus butanica ATCC 21197.
  • 27
    • 33847063873 scopus 로고    scopus 로고
    • trans-1 compounds are 2.7-4.8 kcal/mol more stable than cis-1. In trans-1, an intramolecular hydrogen bond (amide N-H as a proton donor, cyclic N as a proton acceptor) accounts for their extra stabilization in relation to cis-1 compounds.
    • trans-1 compounds are 2.7-4.8 kcal/mol more stable than cis-1. In trans-1, an intramolecular hydrogen bond (amide N-H as a proton donor, cyclic N as a proton acceptor) accounts for their extra stabilization in relation to cis-1 compounds.
  • 29
    • 33847034780 scopus 로고    scopus 로고
    • Absorbance or optical density at 650 nm
    • Absorbance or optical density at 650 nm.
  • 31
    • 33847060871 scopus 로고    scopus 로고
    • In a complementary experiment, R. rhodochrous was grown in the presence of diethyl phosphoramidate (an amidase inhibitor11, suspended in the usual phosphate buffer with an A650 of only 0.30, and then exposed to (±)-l-benzylaziridine-2-carbonitrile (2a) during 34 min. From the crude product (a 56:44 mixture of 2a/1a; crude yield, 90, we were able to isolate the amide (1S,2R)-1a with 8% ee. Therefore, the nitrile hydratase has a poor 2R-selectivity, the same as the amidase's high 2R-selectivity. This observation accounts for the fact that the yields in (1R,2S)-1 obtained from (±)-2 were slightly lower than those obtained from (±)-1
    • 650 of only 0.30, and then exposed to (±)-l-benzylaziridine-2-carbonitrile (2a) during 34 min. From the crude product (a 56:44 mixture of 2a/1a; crude yield, 90%), we were able to isolate the amide (1S,2R)-1a with 8% ee. Therefore, the nitrile hydratase has a poor 2R-selectivity, the same as the amidase's high 2R-selectivity. This observation accounts for the fact that the yields in (1R,2S)-1 obtained from (±)-2 were slightly lower than those obtained from (±)-1.
  • 32
    • 0343447952 scopus 로고    scopus 로고
    • See ref 5c and also: Lambert, C.; Viehe, H. G. Tetrahedron Lett. 1985, 26, 4439-4442. In ref 5e, such acids have to be formed, but no comment is made about them.
    • See ref 5c and also: Lambert, C.; Viehe, H. G. Tetrahedron Lett. 1985, 26, 4439-4442. In ref 5e, such acids have to be formed, but no comment is made about them.
  • 33
    • 12444272862 scopus 로고
    • and references therein
    • Singh, S. P.; Kagan, J. J. Org. Chem. 1970, 35, 2203-2207 and references therein.
    • (1970) J. Org. Chem , vol.35 , pp. 2203-2207
    • Singh, S.P.1    Kagan, J.2
  • 39
    • 33847046353 scopus 로고    scopus 로고
    • 1H NMR spectra with those of the corresponding aziridineamides 1.
    • 1H NMR spectra with those of the corresponding aziridineamides 1.
  • 43
    • 0032538362 scopus 로고    scopus 로고
    • For a review, see: Lucet, D.; Le Gall, T.; Mioskowski, C. Angew. Chem., Int. Ed. 1998, 37, 2580-2627.
    • For a review, see: Lucet, D.; Le Gall, T.; Mioskowski, C. Angew. Chem., Int. Ed. 1998, 37, 2580-2627.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.