Highly Enantioselective Reduction of Carbonyl Compounds Using a Reductase Purified from Bakers' Yeast

Tadashi Ema, Yasushi Sugiyama, Minoru Fukumoto, Hiroyuki Moriya, Jing Nan Cui, Takashi Sakai, Masanori Utaka

Research output: Contribution to journalArticle

42 Citations (Scopus)

Abstract

An NADPH-dependent reductase that shows reducing activity for 1-chloro-2-hexanone has been purified from bakers' yeast. SDS-PAGE and gel filtration suggested that the purified reductase is a monomeric enzyme with a molecular weight of ca. 37 kDa. Asymmetric reduction of several carbonyl compounds using the purified reductase has been carried out. 1-Chloro-2-hexanone, 1-acetoxy-2-heptanone, methyl acetoacetate, ethyl pyruvate, 1-chloro-2,4-pentanedione, and 2,4-hexanedione were reduced to the corresponding alcohols with high enantiomeric purities (>98% ee). The reductase showed high specificity constants (kcat/Km = 103-105 s-1 M-1) and relatively low Michaelis constants (Km = 10-4-10-3 M) for all the substrates examined.

Original languageEnglish
Pages (from-to)4996-5000
Number of pages5
JournalJournal of Organic Chemistry
Volume63
Issue number15
Publication statusPublished - Jul 24 1998

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Carbonyl compounds
Yeast
Methyl n-Butyl Ketone
Oxidoreductases
NADP
Gels
Molecular weight
Alcohols
Substrates
Enzymes

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Ema, T., Sugiyama, Y., Fukumoto, M., Moriya, H., Cui, J. N., Sakai, T., & Utaka, M. (1998). Highly Enantioselective Reduction of Carbonyl Compounds Using a Reductase Purified from Bakers' Yeast. Journal of Organic Chemistry, 63(15), 4996-5000.

Highly Enantioselective Reduction of Carbonyl Compounds Using a Reductase Purified from Bakers' Yeast. / Ema, Tadashi; Sugiyama, Yasushi; Fukumoto, Minoru; Moriya, Hiroyuki; Cui, Jing Nan; Sakai, Takashi; Utaka, Masanori.

In: Journal of Organic Chemistry, Vol. 63, No. 15, 24.07.1998, p. 4996-5000.

Research output: Contribution to journalArticle

Ema, T, Sugiyama, Y, Fukumoto, M, Moriya, H, Cui, JN, Sakai, T & Utaka, M 1998, 'Highly Enantioselective Reduction of Carbonyl Compounds Using a Reductase Purified from Bakers' Yeast', Journal of Organic Chemistry, vol. 63, no. 15, pp. 4996-5000.
Ema T, Sugiyama Y, Fukumoto M, Moriya H, Cui JN, Sakai T et al. Highly Enantioselective Reduction of Carbonyl Compounds Using a Reductase Purified from Bakers' Yeast. Journal of Organic Chemistry. 1998 Jul 24;63(15):4996-5000.
Ema, Tadashi ; Sugiyama, Yasushi ; Fukumoto, Minoru ; Moriya, Hiroyuki ; Cui, Jing Nan ; Sakai, Takashi ; Utaka, Masanori. / Highly Enantioselective Reduction of Carbonyl Compounds Using a Reductase Purified from Bakers' Yeast. In: Journal of Organic Chemistry. 1998 ; Vol. 63, No. 15. pp. 4996-5000.
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