63393-59-9

Basic information

• Product Name: ACETYL-D-HOMOPHENYLALANINE
• Synonyms: ACETYL-D-HOMOPHENYLALANINE;AC-D-HOPHE-OH;AC-D-HPH-OH;(R)-2-(AC-AMINO)-4-PHENYLBUTYRIC ACID;N-Acetyl-D-homophenylalanine;(R)-2-acetamido-4-phenylbutanoic acid;Ac-D-HomoPhe-OH;Acetyl-D-homophenylalanine≥ 99% (HPLC)
• CAS NO: 63393-59-9
• Molecular Formula: C₁₂H₁₅NO₃
• Molecular Weight: 221.25
• Mol File: 63393-59-9.mol

Chemical Properties

• Boiling Point: 461.1°C at 760 mmHg
• Flash Point: 232.6°C
• Appearance: /
• Density: 1.169g/cm³
• Vapor Pressure: 2.68E-09mmHg at 25°C
• Refractive Index: 1.541
• Storage Temp.: 2-8°C
• CAS DataBase Reference: ACETYL-D-HOMOPHENYLALANINE(CAS DataBase Reference)
• NIST Chemistry Reference: ACETYL-D-HOMOPHENYLALANINE(63393-59-9)
• EPA Substance Registry System: ACETYL-D-HOMOPHENYLALANINE(63393-59-9)

Safety Data

• Hazardous Substances Data: 63393-59-9(Hazardous Substances Data)

Usage

Chemical Properties

White crystals

InChI:InChI=1/C12H15NO3/c1-9(14)13-11(12(15)16)8-7-10-5-3-2-4-6-10/h2-6,11H,7-8H2,1H3,(H,13,14)(H,15,16)/t11-/m1/s1

Upstream product

• 5440-40-4 2-(acetylamino)-4-phenylbutanoic acid 
• 36061-01-5 (+/-)-N-acetylhomophenylalanine methyl ester 
• 120379-81-9 5-phenylethyl-imidazolidine-2,4-dione 
• 1012-05-1 D,L-homophenylalanine 
• 4263-93-8 2-hydroxy-4-phenylbutanoic acid 
• 710-11-2 2-oxo-4-phenylbutyric acid 
• 768-56-9 4-Phenylbut-1-ene 
• 124888-60-4 4-phenylbutane-1,2-diol 
• 82795-51-5 D-homophenylalanine 

Downstream Products

• 82795-51-5 D-homophenylalanine 
• 117560-24-4 p-tolylsulfonic caid salt of D-homophenylalanine benzyl ester 

Relevant articles and documents

Direct Synthesis of Free α-Amino Acids by Telescoping Three-Step Process from 1,2-Diols

A practical telescoping three-step process for the syntheses of α-amino acids from the corresponding 1,2-diols has been developed. This process enables the direct synthesis of free α-amino acids without any protection/deprotection step. This method was also effective for the preparation of a 15N-labeled α-amino acid. 1,2-Diols bearing α,β-unsaturated ester moieties afforded bicyclic α-amino acids through intramolecular [3 + 2] cycloadditions. A preliminary study suggests that the resultant α-amino acids are resolvable by aminoacylases with almost complete selectivity.

Preparation of cross-linked enzyme aggregates of l-aminoacylase via co-aggregation with polyethyleneimine

l-Aminoacylase from Aspergillus melleus was co-aggregated with polyethyleneimine and subsequently cross-linked with glutaraldehyde to obtain aminoacylase-polyethyleneimine cross-linked enzyme aggregates (termed as AP-CLEA). Under the optimum conditions, AP-CLEA expressed 74.9% activity recovery and 81.2% aggregation yield. The said method of co-aggregation and cross-linking significantly improved the catalytic stability of l-aminoacylase with respect to temperature and storage. AP-CLEA were employed for enantioselective synthesis of three unnatural amino acids (namely: phenylglycine, homophenylalanine and 2-naphthylalanine) via chiral resolution of their ester-, amide- and N-acetyl derivatives. The enantioselectivity of AP-CLEA was the highest for hydrolysis of amino acid amides; was moderate for hydrolysis of N-acetyl amino acids and was the least for hydrolysis of amino acid esters. Furthermore, AP-CLEA were found to retain more than 92% of the initial activity after five consecutive batches of (RS)-homophenylalanine hydrolysis suggesting an adequate operational stability of the biocatalyst.

Enzymatic resolution of N-acetyl-homophenylalanine with mammalian kidney acetone powders

Kidney acetone powders (KAP) from beef, dog, hog, rat, and sheep have been evaluated for resolving N-acetyl-DL-homophenylalanine. We also propose a simple protocol for the preparation of both enantiomers of homophenylalanine by enzymatic resolution using mammalian KAP. The beef kidney afforded the best results, rendering the highest isolated yields, 37.5% and 41% and enantiomeric excesses of 94% and 99% for both D-N-Ac-homophenylalanine and L-homophenylalanine, respectively.

A novel tea-bag methodology for enzymatic resolutions of α-amino acid derivatives in reverse micellar media

A novel tea bag methodology for resolution of methyl esters of N-acetyl- α-amino acids in reverse micellar medium of bis(2-ethylhexyl) sulfosuccinate sodium salt (AOT) in isooctane-chloroform using immobilized enzymes or microbial cells is presented. The methodology effectively solves the problems of substrate solubility, product separation and surfactant recycling and provides products in high yields (80 to 90%) and excellent optical purities (% ee 97 to >99%).

Studies on angiotensin converting enzyme inhibitors. VI. Synthesis and angiotensin converting enzyme inhibitory activities of the dicarboxylic acid derivative of imidapril and its diastereoisomers

All possible diastereoisomers of the dicarboxylic acid (10a), the biologically active form of imidapril (1), were synthesized, and their inhibitory activity against angiotensin converting enzyme (ACE) was examined. The in vitro ACE inhibitory activity of these compounds greatly depended on the configurations of the three asymmetric carbons in each molecule. The (S,S,S) isomer (10a) showed much more potent activity than the others.