ETHYL BENZYLPYRUVATE

CCOC(=O)C(=O)CCC1=CC=CC=C1

InChIKey=STPXIOGYOLJXMZ-UHFFFAOYSA-N

InChI=1S/C12H14O3/c1-2-15-12(14)11(13)9-8-10-6-4-3-5-7-10/h3-7H,2,8-9H2,1H3

Ethyl 2-oxo-4-phenylbutyrate is useful for the synthesis of the important chiral precursor for angiotensin-converting enzyme (ACE) inhibitors.

Targets

Primary Target	Pharmacology	Condition	Potency
Reductase CgKR2 (Candida glabrata) 1 Target ID: Reductase CgKR2 (Candida glabrata) Sources: https://www.ncbi.nlm.nih.gov/pubmed/22480179	Substrate 661
NADPH-dependent alpha-keto amide reductase 1 Target ID: Q07551 Gene ID: 851433.0 Gene Symbol: NA Target Organism: Saccharomyces cerevisiae (strain ATCC 204508 / S288c) (Baker's yeast) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15469278	Substrate 661
Putative reductase 1 1 Target ID: Q12458 Gene ID: 851974.0 Gene Symbol: YPR1 Target Organism: Saccharomyces cerevisiae (strain ATCC 204508 / S288c) (Baker's yeast) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15469278	Substrate 661
Putative 2-hydroxyacid dehydrogenase YGL185C 1 Target ID: P53100 Gene ID: 852690.0 Gene Symbol: NA Target Organism: Saccharomyces cerevisiae (strain ATCC 204508 / S288c) (Baker's yeast) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15469278	Substrate 661

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Efficient synthesis of a chiral precursor for angiotensin-converting enzyme (ACE) inhibitors in high space-time yield by a new reductase without external cofactors.	2012 Apr 20	22480179
Scalable biocatalytic synthesis of optically pure ethyl (R)-2-hydroxy-4-phenylbutyrate using a recombinant E. coli with high catalyst yield.	2013 Dec	24120725
Semi-rational engineering of a thermostable aldo-keto reductase from Thermotoga maritima for synthesis of enantiopure ethyl-2-hydroxy-4-phenylbutyrate (EHPB).	2017 Jun 21	28638047

Patents

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Gox0525 showed useful specificity for 2-oxo-4-phenylbutyrate, with kcat/Km values of 1.719 × 10(4) M−1 s−1.

Name

Type

Language

ETHYL BENZYLPYRUVATE

Systematic Name

English

ETHYL PHENETHYLOXALATE

Common Name

English

2-OXO-4-PHENYLBUTANOIC ACID ETHYL ESTER

Systematic Name

English

ETHYL 2-OXO-4-PHENYLBUTANOATE

Systematic Name

English

Code System Code Type Description

CAS

64920-29-2