(2S,3R)-methyl-2-benzamidomethyl-3-hydroxybutyrate → Methyl 2-((benzoylamino)methyl)-3-oxobutanoate

HRID 874144

Reaction equation

HRID 874144 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C@@H:4]([CH2:8][NH:9][C:10](=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C@H:5]([OH:7])[CH3:6].COC(=O)[C@H](CNC(=O)C1C=CC=CC=1)[C@H](O)C>>[CH3:1][O:2][C:3](=[O:18])[CH:4]([CH2:8][NH:9][C:10](=[O:17])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:5](=[O:7])[CH3:6]

Participants

3

Reactant 2

HCID 10060699(2S,3R)-methyl-2-benzamidomethyl-3-hydroxybutyrateHCID 10399905(2R,3R)-methyl-2-benzamidomethyl-3-hydroxybutyrate

Product 1

HCID 11831808Methyl 2-((benzoylamino)methyl)-3-oxobutanoate

Procedure

The ADH-LK variant with SEQ ID No. 90 was used for further evolution of an efficient KRED for production of (2S,3R)-methyl-2-benzamidomethyl-3-hydroxybutyrate. Similarly, an ADH-LK variant with SEQ ID No.94 containing 10 mutations compared to ADH-LK which gave primarily the (2R,3R) stereoisomer, was used for further evolution of an efficient KRED for production of (2R,3R)-methyl-2-benzamidomethyl-3-hydroxybutyrate.

Workup

  1. additionSimilarly, an ADH-LK variant with SEQ ID No.94 containing 10 mutations
  2. customgave primarily the (2R,3R) stereoisomer

Sources & evidence

ORD record
ord-624b4080a11c4acd9ec352edac3272ec
Source dataset
uspto-grants-2015_03
Patent number
US08980606B2

Linked notes

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