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Substrate Report for: W22-methyl-ester

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, Not A/B H target, Drug, Pro-Drug
Chemical_Nomenclature methyl 2-[(2S)-4-methyl-3-oxo-2,5-dihydro-1H-1,4-benzodiazepin-2-yl]acetate
Canonical SMILES CN1CC2=CC=CC=C2NC(C1=O)CC(=O)OC
InChI InChI=1S/C13H16N2O3/c1-15-8-9-5-3-4-6-10(9)14-11(13(15)17)7-12(16)18-2/h3-6,11,14H,7-8H2,1-2H3/t11-/m0/s1
InChIKey OCJURJNFLYOSLL-NSHDSACASA-N
Other name(s)
________________________________________________________________________________________________
MW|248.27
Formula|C13H16N2O3
CAS_number|
PubChem|11322612
UniChem|OCJURJNFLYOSLL-NSHDSACASA-N
IUPHAR|
Wikipedia|

Target
Families | W22-methyl-ester ligand of proteins in family: Bacterial_esterase, Canar_LipB

References:
Search PubMed for references concerning: W22-methyl-ester
    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 NJ, Seago A, Carey JS, Freer R, Preston C, Lye GJ
    Ref: Green Chem, 6:475 , 2004 : PubMed

            

    Title: The atomic-resolution structure of a novel bacterial esterase
    Bourne PC, Isupov MN, Littlechild JA
    Ref: Structure Fold Des, 8:143, 2000 : PubMed