SE-Phenyl-L-selenocysteine

Base Information

• Chemical Name: SE-Phenyl-L-selenocysteine
• CAS No.: 71128-82-0
• Molecular Formula: C9H11NO2Se
• Molecular Weight: 244.152
• Hs Code.: 2922499990
• European Community (EC) Number: 621-362-1
• DSSTox Substance ID: DTXSID40431490
• Nikkaji Number: J747.445H
• Wikidata: Q72498728
• ChEMBL ID: CHEMBL62587
• Mol file: 71128-82-0.mol

Synonyms:SE-PHENYL-L-SELENOCYSTEINE;71128-82-0;(2R)-2-amino-3-phenylselanylpropanoic acid;CID 9834704;3-(Phenylseleno)alanine;CHEMBL62587;SCHEMBL1158086;DTXSID40431490;AKOS005145550

Chemical Property of SE-Phenyl-L-selenocysteine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 176-177℃
• Boiling Point: 378.689 °C at 760 mmHg
• Flash Point: 182.825 °C
• PSA: 63.32000
• LogP: 0.54660
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 244.99550
• Heavy Atom Count: 13
• Complexity: 169

Purity/Quality:

99.3% ^*data from raw suppliers

Se-Phenyl-L-selenocysteine 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N
• Hazard Codes: T,N
• Statements: 23/25-33-50/53
• Safety Statements: 20/21-28-45-60-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)[Se]CC(C(=O)O)N
• Isomeric SMILES: C1=CC=C(C=C1)[Se]C[C@@H](C(=O)O)N

Technology Process of SE-Phenyl-L-selenocysteine

There total 5 articles about SE-Phenyl-L-selenocysteine 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:

2-amino-3-chloropropanoic acid (2731-73-9) + diphenyl diselenide (1666-13-3) → L-(Se)-phenylselenocysteine (71128-82-0)

Guidance literature:

With sodium hydroxide; sodium tetrahydroborate; Yield given. Multistep reaction; 1.) EtOH, from 0 deg C to RT, 2.) EtOH, RT, 3 h;

DOI:10.1021/jm950750x

Reference yield:

(S)-2-tert-butoxycarbonylamino-3-phenylselanylpropionic acid (179087-83-3) → L-(Se)-phenylselenocysteine (71128-82-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1039/b505299h

Reference yield:

O-acetyl-L-serine (5147-00-2,25248-96-8,44901-25-9) + Benzeneselenol (645-96-5) → L-(Se)-phenylselenocysteine (71128-82-0)

Guidance literature:

With pyridoxal 5'-phosphate; cysteine synthase from Escherichia coli; In aq. phosphate buffer; at 37 ℃; pH=6.4 - 7; Enzymatic reaction;

DOI:10.1002/anie.202014540

upstream raw materials:

2-amino-3-chloropropanoic acid

diphenyl diselenide

(S)-2-tert-butoxycarbonylamino-3-phenylselanylpropionic acid

(R)-methyl 2-(tert-butoxycarbonylamino)-3-(phenylselanyl)propanoate

Downstream raw materials:

N-(9-fluorenylmethoxycarbonyl)-L-β-phenylselenocysteine

Ac-GLPU(Ph)VIA

LU(Ph)PGC(Trt)VG

Fmoc-GLPU(Ph)VIA

Refernces

• 1、 Wang, Yong,Chen, Xiaoxu,Cai, Wenkang,Tan, Linzhi,Yu, Yutong,Han, Boyang,Li, Yuxuan,Xie, Yuanzhe,Su, Yeyu,Luo, Xiaozhou,Liu, Tao. "Expanding the Structural Diversity of Protein Building Blocks with Noncanonical Amino Acids Biosynthesized from Aromatic Thiols". supporting information. p. 10040 - 10048. Retrieved 2021/03/26.
• 2、 Just-Baringo, Xavier,Bruno, Paolo,Ottesen, Lars K.,Canedo, Librada M.,Albericio, Fernando,Alvarez, Mercedes. "Total synthesis and stereochemical assignment of baringolin". . p. 7818 - 7821. Retrieved 2013/08/23.