4.4 Article

Biocatalytic synthesis of chiral five-membered carbasugars intermediates utilizing CV2025 w-transaminase from Chromobacterium violaceum

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JOURNAL OF BIOSCIENCE AND BIOENGINEERING
卷 135, 期 5, 页码 369-374

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SOC BIOSCIENCE BIOENGINEERING JAPAN
DOI: 10.1016/j.jbiosc.2023.02.009

关键词

Biocatalysis; Chromobacterium violaceum; CV2025 w-transaminase; Five-membered carbasugars; (S)-4-(Hydroxymethyl)cyclopent-2-enone

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In this study, CV2025 u-transaminase from Chromobacterium violaceum was successfully cloned, expressed, purified, and characterized. The enzyme showed a preference for the R configuration, contrary to the conventional S preference. The highest activity was observed at temperatures below 60 degrees C and at pH 7.5. The study provides a promising strategy for the economic and efficient synthesis of chiral five-membered carbasugars.
(S)-4-(Hydroxymethyl)cyclopent-2-enone is a key intermediate in the synthesis of chiral five-membered carbasugars, which can be used to synthesize a large number of pharmacologically relevant carbocyclic nucleosides. Herein, CV2025 u-transaminase from Chromobacterium violaceum was selected based on substrate similarity to convert ((1S,4R)-4-aminocyclopent-2-enyl)methanol to (S)-4-(hydroxymethyl)cyclopent-2-enone. The enzyme was successfully cloned, expressed in Escherichia coli, purified and characterized. We show that it has R configuration preference in contrast with the conventional S preference. The highest activity was obtained below 60 degrees C and at pH 7.5. Cations Ca2+ and K+ enhanced activity by 21% and 13%, respectively. The conversion rate reached 72.4% within 60 min at 50 degrees C, pH 7.5, using 0.5 mM pyridoxal-5'-phosphate, 0.6 mM CV2025, and 10 mM substrate. The present study provides a promising strategy for preparing five-membered carbasugars economically and efficiently.(c) 2023, The Society for Biotechnology, Japan. All rights reserved.

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