ETHYL BENZYLPYRUVATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H14O3
Molecular Weight	206.2378
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

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

HIDE SMILES / InChI

Molecular Formula	C12H14O3
Molecular Weight	206.2378
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18716813 | https://www.ncbi.nlm.nih.gov/pubmed/22480179

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

Approval Year

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
Systematic investigation of Saccharomyces cerevisiae enzymes catalyzing carbonyl reductions.	2004 Oct 13	15469278
Effect of ionic liquid [BMIM][PF6] on asymmetric reduction of ethyl 2-oxo-4-phenylbutyrate by Saccharomyces cerevisiae.	2008 Nov	18716813
Engineering cofactor preference of ketone reducing biocatalysts: A mutagenesis study on a γ-diketone reductase from the yeast Saccharomyces cerevisiae serving as an example.	2010 Apr 14	20480039
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
A genomic search approach to identify carbonyl reductases in Gluconobacter oxydans for enantioselective reduction of ketones.	2014	25130736
Crystallographic analysis of a novel aldo-keto reductase from Thermotoga maritima in complex with NADP⁺.	2015 Jul	26144229
Cloning, expression, and characterization of an anti-Prelog stereospecific carbonyl reductase from Gluconobacter oxydans DSM2343.	2015 Mar	25659628
Towards the computational design and engineering of enzyme enantioselectivity: A case study by a carbonyl reductase from Gluconobacter oxydans.	2016 Jan 10	26590330
Assessing the stereoselectivity of carbonyl reductases toward the reduction of OPBE and docking analysis.	2016 Jul	25989134
Cloning and characterization of three ketoreductases from soil metagenome for preparing optically active alcohols.	2016 Oct	27383399
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
Genome hunting of carbonyl reductases from Candida glabrata for efficient preparation of chiral secondary alcohols.	2018 Jan	28978494

Patents

Sample Use Guides

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:24:20 GMT 2023` Edited by `admin` on `Fri Dec 15 16:24:20 GMT 2023`
Record UNII	5YNU9LPT51
Record Status	`Validated (UNII)`
Record Version

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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