W22

A precursor of Lotrafiban ( a potent non-peptidic antagonist that inhibits platelet aggregation). The S enantiomer is necessary for activity.Hydrolysis of racemic W22-Acetate by Lipase Novozyme 435 results in only the S isomer product

General

Type : Benzodiazepin,Diazepan,Azepane

Chemical_Nomenclature : 2-[(2S)-4-methyl-3-oxo-2,5-dihydro-1H-1,4-benzodiazepin-2-yl]acetic acid

Canonical SMILES : CN1CC2=CC=CC=C2N[C@H](C1=O)CC(=O)O

InChI : InChI=1S\/C12H14N2O3\/c1-14-7-8-4-2-3-5-9(8)13-10(12(14)17)6-11(15)16\/h2-5,10,13H,6-7H2,1H3,(H,15,16)\/t10-\/m0\/s1

InChIKey : CLWDLBDPVUWYEW-JTQLQIEISA-N

Other name(s) : [(2S)-4-methyl-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepin-2-yl]acetic acid,SCHEMBL8503077,DB08717,(2S)-3(2H)-Oxo-4-methyl-4,5-dihydro-1H-1,4-benzodiazepine-2beta-acetic acid

MW : 234.25

Formula : C12H14N2O3

CAS_number :

PubChem : 11117974

UniChem : CLWDLBDPVUWYEW-JTQLQIEISA-N

IUPHAR :

Wikipedia :

Target

Families : W22 ligand of proteins in family: Bacterial_esterase

Stucture : 2WKW Alcaligenes esterase complexed with product analogue

Protein : alcsp-cxest

References (2)

Title : Lipase catalysed resolution of the Lotrafiban intermediate 2,3,4,5-tetrahydro-4-methyl-3-oxo-1 H-1,4-benzodiazepine-2-acetic acid methyl ester in ionic liquids: comparison to the industrial t-butanol process - Roberts_2004_Green.Chem_6_475

Author(s) : Roberts NJ , Seago A , Carey JS , Freer R , Preston C , Lye GJ

Ref : Green Chem , 6 :475 , 2004

Abstract : Roberts_2004_Green.Chem_6_475

ESTHER : Roberts_2004_Green.Chem_6_475

PubMedSearch : Roberts_2004_Green.Chem_6_475

PubMedID:

Gene_locus related to this paper: canar-LipB

Title : The atomic-resolution structure of a novel bacterial esterase - Bourne_2000_Structure.Fold.Des_8_143

Author(s) : Bourne PC , Isupov MN , Littlechild JA

Ref : Structure Fold Des , 8 :143 , 2000

Abstract : Bourne_2000_Structure.Fold.Des_8_143

ESTHER : Bourne_2000_Structure.Fold.Des_8_143