Realization of the synthesis of α,α-disubstituted carbamylacetates and cyanoacetates by either enzymatic or chemical functional group transformation, depending upon the substrate specificity of Rhodococcus amidase

Tetrahedron Asymmetry

Volumn 15, Issue 18, 2004, Pages 2817-2820

  Yokoyama, Masahiro ^a   Kashiwagi, Mieko ^a   Iwasaki, Masakazu ^a   Fuhshuku, Ken Ichi ^a   Ohta, Hiromichi ^a   Sugai, Takeshi ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ALPHA CYANO ALPHA FLUORO ALPHA PHENYLACETIC ACID; AMIDASE; DIAMIDE; DIETHYL ALPHA FLUORO ALPHA PHENYLMALONATE; FLUORINE; MALONIC ACID DERIVATIVE; MALONONITRILE; METHYLDOPA; NITRILE; NITRILE HYDRATASE; UNCLASSIFIED DRUG;

ARTICLE; ATOM; BACTERIUM TRANSFORMATION; CHIRALITY; ENANTIOSELECTIVITY; ENZYME SPECIFICITY; ENZYME SUBSTRATE; HYDROLYSIS; PRECURSOR; PRIORITY JOURNAL; REACTION ANALYSIS; RHODOCOCCUS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 4644230079     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.04.047     Document Type: Article

References (24)

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2. 1 R. rhodochrous IFO15564 is now available as the strain of NBRC15564 from the NITE Biological Resource Center (NBRC), 2-5-8, Kazusakamatari, Kisarazu, Chiba 292-0818, Japan
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9. The ees were estimated either by the HPLC analyses of 10, 11, or 12. The absolute configuration of the products was determined by the derivation to known 7, the corresponding α-amino acids and/or mutual conversion between the products
10. 6 to avoid the formation of the enzymically inactive 3k
11. 4 buffer solution (pH 2.8)/acetonitrile = 3/2; flow rate, 1.0 mL/min; detection at 254 nm]. 7.5 min (2-naphthylamide), 8.3 min (2k), and 15.4 min (2-naphthylacetic acid). The conversion of 1-naphthylamide to 2-naphthylacetic acid was 17% at 30 min in the presence of 2k, while 60% conversion was recorded in the control experiment. The relative activity under the influence of 2k was 28%. In a similar manner, the activity decreased to 70% by 3k
12. 2O except for the quick exchange of amide protons
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21. Compound 3k: Colorless needles, mp 224-225°C
22. 2O, 6%), 135 (100%), 108 (97%), 77 (5%), 44 (64%)
23. 15b
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