D-Homophenylalanine

Base Information

• Chemical Name: D-Homophenylalanine
• CAS No.: 82795-51-5
• Molecular Formula: C10H13NO2
• Molecular Weight: 179.219
• Hs Code.: 29224999
• European Community (EC) Number: 853-256-8
• UNII: 5847ZW3PEP
• Nikkaji Number: J36.249B
• Wikidata: Q27261551
• Mol file: 82795-51-5.mol

Synonyms:D-Homophenylalanine;82795-51-5;(2R)-2-amino-4-phenylbutanoic acid;h-d-hophe-oh;(R)-2-amino-4-phenylbutanoic acid;(r)-homophenylalanine;Homophenylalanine, D-;h-d-homophe-oh;Homophenylalanine, (-)-;D-2-amino-4-phenylbutanoic acid;d-homophenyl-ala;(R)-2-Amino-4-phenylbutyric acid;UNII-5847ZW3PEP;5847ZW3PEP;Benzenebutanoic acid, alpha-amino-, (alphaR)-;(2R)-2-azaniumyl-4-phenylbutanoate;(-)-2-Amino-4-phenylbutyric acid;MFCD00063091;2-amino-4-phenyl-butyric acid;(r)-2-amino-4-phenyl-butyric acid;d-homophenyl alanine;3-Benzyl-D-Ala-OH;SCHEMBL44312;JTTHKOPSMAVJFE-SECBINFHSA-N;AKOS015853803;AC-9968;CS-W017272;D-Homophenylalanine, >=98.0% (HPLC);DS-14385;AM20041216;H0984;EN300-144880;J-640375;Q27261551;Z1255399095;BENZENEBUTANOIC ACID, .ALPHA.-AMINO-, (.ALPHA.R)-

Chemical Property of D-Homophenylalanine

Chemical Property:

• Appearance/Colour: Beige powder
• Vapor Pressure: 9.79E-05mmHg at 25°C
• Melting Point: 300 °C
• Refractive Index: -45 ° (C=1, 3mol/L HCl)
• Boiling Point: 324.8 °C at 760 mmHg
• PKA: 2.32±0.10(Predicted)
• Flash Point: 150.2 °C
• PSA: 63.32000
• Density: 1.164 g/cm³
• LogP: 1.73140
• Storage Temp.: Store at RT.
• Solubility.: Aqueous Acid (Sparingly), Aqueous Base (Slightly)
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 179.094628657
• Heavy Atom Count: 13
• Complexity: 164

Purity/Quality:

99% ^*data from raw suppliers

D-Homophenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CCC(C(=O)O)N
• Isomeric SMILES: C1=CC=C(C=C1)CC[C@H](C(=O)O)N
• Uses: D-Homophenylalanine is used in peptide synthesis as an amino acid protection monomer.

Technology Process of D-Homophenylalanine

There total 43 articles about D-Homophenylalanine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

trans-2-phenylvinylboronic acid (6783-05-7) + (2S)-2-phenylglycinol (20989-17-7) + glyoxalic acid monohydrate (6000-59-5,1152495-30-1) → D-homophenylalanine (82795-51-5)

Guidance literature:

In dichloromethane;

Reference yield: 91.0%

(3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-(2'-oxo-2'-phenylethyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (100516-57-2) → D-homophenylalanine (943-73-7) + D-homophenylalanine (82795-51-5)

Guidance literature:

With hydrogen; palladium dichloride; In tetrahydrofuran; ethanol; for 34h; under 2068.6 Torr; Yields of byproduct given;

DOI:10.1021/ja00213a031

Reference yield: 50.0%

2-(acetylamino)-4-phenylbutanoic acid (5440-40-4) → D-homophenylalanine (82795-51-5) + (R)-2-Acetamido-4-phenylbutansaeure (96613-91-1)

Guidance literature:

With D-aminoacylase; cobalt(II) chloride; In aq. buffer; at 20 - 38 ℃; for 5h; pH=7.5; enantioselective reaction; Inert atmosphere; Resolution of racemate; Enzymatic reaction;

DOI:10.1021/acs.orglett.8b03910

upstream raw materials:

(R)-homophenylalanine amide

(2R)-N-acetyl-2-amino-4-phenylbutyric acid

(2R,5R)-2-t-butyl-1-t-butyloxycarbonyl-3-methyl-5-(2-phenylethyl)-4-imidazolidinone

(3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-(2'-oxo-2'-phenylethyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

Downstream raw materials:

(2R)-N-acetyl-2-amino-4-phenylbutyric acid

Cbz-D-homoPhe-OH

1-(1,1-dimethylethyl)-(7S,10S,12E,16R)-4,4-dimethyl-10-<(1R,2E)-1-methyl-3-phenyl-2-propenyl>-7-(2-methylpropyl)-5,8,14-trioxo-16-(2-phenylethyl)-6,9-dioxa-2,15-diazaheptadec-12-enedioate

(R)-2-bromo-4-phenylbutyric acid

Refernces

• 1、 Li, Jianjiong,Wang, Yingang,Wu, Qiaqing,Yao, Peiyuan,Yu, Shanshan,Zhu, Dunming. "Simultaneous Preparation of (S)-2-Aminobutane and d -Alanine or d -Homoalanine via Biocatalytic Transamination at High Substrate Concentration". supporting information. . Retrieved 2022/03/01.
• 2、 Heuson, Egon,Charmantray, Franck,Petit, Jean-Louis,de Berardinis, Véronique,Gefflaut, Thierry. "Enantioselective Synthesis of d- and l-α-Amino Acids by Enzymatic Transamination Using Glutamine as Smart Amine Donor". supporting information. p. 778 - 785. Retrieved 2019/01/04.