3-Selenoalanine

Base Information

• Chemical Name: 3-Selenoalanine
• CAS No.: 10236-58-5
• Deprecated CAS: 18312-66-8
• Molecular Formula: C₃H₇NO₂Se
• Molecular Weight: 168.054
• European Community (EC) Number: 808-428-7
• DSSTox Substance ID: DTXSID90863222
• Wikipedia: Selenocysteine
• Mol file: 10236-58-5.mol

Synonyms:3-Selenoalanine;DL-Selenocysteine;3-Selenyl-DL-alanine;3614-08-2;SELENO-(DL)-CYSTEINE;HSDB 3534;2-Amino-3-hydroselenopropanoic acid;Selenium-cystine;d,l-Selenocysteine;3-selanylalanine;(S)-2-Amino-3-hydroselenopropanoic acid;Selenocystein;Selenozystein;10236-58-5;Alanine, 3-seleno-;SCHEMBL38519;CHEBI:9093;DTXSID90863222;Alanine, 3-selenyl-, (+-)-;CHEBI:177792;2-Amino-3-hydroselenopropanoicacid;AKOS006276195;LS-16216

Chemical Property of 3-Selenoalanine

Chemical Property:

• Boiling Point: 440.2 °C at 760 mmHg
• PKA: 5.2(at 25℃)
• Flash Point: 220 °C
• PSA: 63.32000
• LogP: -0.20210
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 167.95638
• Heavy Atom Count: 7
• Complexity: 75.3

Purity/Quality:

98%,99%, ^*data from raw suppliers

SELENOCYSTINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Amino Acids and Derivatives
• Canonical SMILES: C(C(C(=O)O)N)[Se]
• Uses: L-Selenocysteine is used in the modulation of oxidative stress through detoxification of biological oxidants as well as repair of oxidized residues.

Technology Process of 3-Selenoalanine

There total 5 articles about 3-Selenoalanine 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: 88.36%

seleno-L-cystine (1464-43-3,2897-21-4,26932-45-6,29621-88-3) → L-selenocysteine (3614-08-2,10236-58-5,18312-66-8,176300-66-6)

Guidance literature:

With sodium tetrahydroborate; sodium hydroxide; In water; at 10 ℃;

Reference yield:

C12H16N2O6Se → L-selenocysteine (3614-08-2,10236-58-5,18312-66-8,176300-66-6)

Guidance literature:

Irradiation;

DOI:10.1021/acschembio.0c00147

Reference yield:

1,5-dihydro-riboflavin (13345-95-4,78692-23-6) + seleno-L-cystine (1464-43-3,2897-21-4,26932-45-6,29621-88-3) → L-selenocysteine (3614-08-2,10236-58-5,18312-66-8,176300-66-6) + riboflavin (83-88-5,482-11-1,482-12-2,3687-62-5,5978-87-0,13123-37-0,33210-89-8,35919-91-6,53187-51-2,53187-52-3,135681-43-5,42880-33-1)

Guidance literature:

In aq. phosphate buffer; at 25 ℃; for 6h; pH=7; pH-value; Equilibrium constant;

DOI:10.1002/kin.21430

upstream raw materials:

seleno-L-cystine

selenodjenkolic acid

1,5-dihydro-riboflavin

Downstream raw materials:

1,5-dihydro-riboflavin

seleno-L-cystine

L-alanin

para-nitrobenzenethiol

Refernces

• 1、 Sun, Qi,Yang, Shu-Hou,Wu, Lei,Dong, Qing-Jian,Yang, Wen-Chao,Yang, Guang-Fu. "Detection of Intracellular Selenol-Containing Molecules Using a Fluorescent Probe with Near-Zero Background Signal". . p. 6084 - 6091. Retrieved 2016.
• 2、 Nehzati, Susan,Dolgova, Natalia V.,Sokaras, Dimosthenis,Kroll, Thomas,Cotelesage, Julien J. H.,Pickering, Ingrid J.,George, Graham N.. "A Photochemically Generated Selenyl Free Radical Observed by High Energy Resolution Fluorescence Detected X-ray Absorption Spectroscopy". . p. 10867 - 10872. Retrieved 2018.
• 3、 Pentelute, Brad L.,Gates, Zachary P.,Tereshko, Valentina,Dashnau, Jennifer L.,Vanderkooi, Jane M.,Kossiakoff, Anthony A.,Kent, Stephen B. H.. "X-ray structure of snow flea antifreeze protein determined by racemic crystallization of synthetic protein enantiomers". . p. 9695 - 9701. Retrieved 2008.
• 4、 Mondal, Santanu,Mugesh, Govindasamy. "Dehalogenation of Halogenated Nucleobases and Nucleosides by Organoselenium Compounds". . p. 1773 - 1780. Retrieved 2019.
• 5、 Seebeck, Florian P.,Szostak, Jack W.. "Ribosomal synthesis of dehydroalanine-containing peptides". . p. 7150 - 7151. Retrieved 2006.