Production of (2R,3S)-2-Benzamidomethyl-3-Hydroxybutanoates by Immobilized Plant Cells of Parthenocissus Tricuspidata

Hatsuyuki Hamada,Kei Shimoda,Hiroki Hamada,Siddiqi M Shafi,Tatsunari Kobayashi,Naoji Kubota,Nobuyoshi Nakajima

doi:10.4137/bci.s961

Abstract

Incubation of methyl 2-benzamidomethyl-3-oxobutanoate with cultured plant cells of Parthenocissus tricuspidata for 2 days afforded methyl (2 R,3 S)-2-benzamidomethyl-3-hydroxybutanoate with 100% de and >99% ee in 51% yield. The use of immobilized cells of P. tricuspidata in calcium alginate gel improved the yield of the product (95% yield) with 100% de and >99% ee. The immobilized cells of P. tricuspidata maintained the high potential for the reduction of methyl 2-benzamidomethyl-3-oxobutanoate (85% yield) after 5 times of usage.

Highlights

Chiral 2-benzamidomethyl-3-hydroxybutanoates are useful chiral building blocks for asymmetric synthesis of biologically active compounds; optically active 2-benzamidomethyl-3-hydroxybutanoates are chiral synthons for carbapenems.[1,2] Diastereoselective reduction of 2-benzamidomethyl3-oxobutanoates is an attractive method for the production of optically enriched 2-benzamidomethyl3-hydroxybutanoates
We report the high production of methyl (2R,3S)-2-benzamidomethyl-3-hydroxybutanoate by the reduction of methyl 2-benzamidomethyl3-oxobutanoate with immobilized cells of P. tricuspidata in calcium alginate gel
It was found that cultured P. tricuspidata cells were able to reduce 1 to methyl (2R,3S)-2-benzamidomethyl-3-hydroxybutanoate (2), with excellent diastereo- and enantioselectivities

Summary

Introduction

Chiral 2-benzamidomethyl-3-hydroxybutanoates are useful chiral building blocks for asymmetric synthesis of biologically active compounds; optically active 2-benzamidomethyl-3-hydroxybutanoates are chiral synthons for carbapenems.[1,2] Diastereoselective reduction of 2-benzamidomethyl3-oxobutanoates is an attractive method for the production of optically enriched 2-benzamidomethyl3-hydroxybutanoates. Microbial reduction of 2-methyl-3-oxobutanoate to give a mixture of syn- and anti- 3-hydroxy-2-methylbutanoate.[3,4,5,6] little attention has been paid to the diastereoand enantioselectivity in the reduction of 2-benzamidomethyl-3-oxobutanoates by cultured plant cells. There have been no reports on the large scale production of 2-benzamidomethyl3-hydroxybutanoates by immobilized plant cells.[7] We report the high production of methyl (2R,3S)-2-benzamidomethyl-3-hydroxybutanoate by the reduction of methyl 2-benzamidomethyl3-oxobutanoate with immobilized cells of P. tricuspidata in calcium alginate gel

Methods

Results

Conclusion