1464-43-3

Basic information

• Product Name: 2-amino-3-(2-amino-2-carboxy-ethyl)selanylselanyl-propanoic acid
• Synonyms: 2-amino-3-(2-amino-2-carboxy-ethyl)selanylselanyl-propanoic acid;Selenocystine;3,3'-(Diseleno)bis(L-alanine);3,3'-Diselenobis(L-alanine);3,3'-Diselenobisalanine;Selenium cystine
• CAS NO: 1464-43-3
• Molecular Formula: C₆H₁₂N₂O₄Se₂
• Molecular Weight: 334.12
• Mol File: 1464-43-3.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 108.25°C (estimate)
• Flash Point: 279.3°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 5.12E-13mmHg at 25°C
• CAS DataBase Reference: 2-amino-3-(2-amino-2-carboxy-ethyl)selanylselanyl-propanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-amino-3-(2-amino-2-carboxy-ethyl)selanylselanyl-propanoic acid(1464-43-3)
• EPA Substance Registry System: 2-amino-3-(2-amino-2-carboxy-ethyl)selanylselanyl-propanoic acid(1464-43-3)

Safety Data

• Hazardous Substances Data: 1464-43-3(Hazardous Substances Data)

Usage

Safety Profile

Poison by intraperitoneal route. Mutation data reported. When heated to decomposition it emits very toxic fumes of NOx, and Se. See also SELENIUM COMPOUNDS.

InChI:InChI=1/C6H12N2O4Se2/c7-3(5(9)10)1-13-14-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)

Upstream product

• 19794-48-0 (2R)-serine O-sulfate 
• 25248-96-8 O-acetyl-D-serine 
• 2575-73-7 Se-benzyl-L-selenocysteine 
• 109276-78-0 L-dibenzyl N,N'-di(benzyloxycarbonyl)selenocystinate 
• 739301-12-3 seleno-L-cysteine dimethyl ester 
• 195324-31-3 dimethyl 3,3'-diselanediyl-(2R,2'R)-bis(2-((tertbutoxycarbonyl)amino)propanoate) 
• 51887-89-9 β-chloro-L-alanine hydrochloride 
• 2731-73-9 2-amino-3-chloropropanoic acid 
• 23926-58-1 N,N'-bis(benzyloxycarbonyl)-L-cystine diethyl ester 
• 1148111-64-1 C₃H₆NO₂Se^(1-) 
• 1242409-39-7 hemiselenocystine 
• 3614-08-2 L-selenocysteine 
• 83-88-5 riboflavin 
• 56410-68-5 3-chloro-DL-alanine methyl ester 

Downstream Products

• 2575-73-7 2-amino-3-benzylselanyl-propionic acid 
• 3614-08-2 L-selenocysteine 
• 877754-71-7 (2R,2'R)-3,3'-diselanediylbis(2-((tert-butoxycarbonyl)amino)propanoic acid) 
• 27025-41-8 Oxidized glutathione 
• 188609-44-1 C₁₃H₂₂N₄O₈SSe 
• 40055-98-9 oxidized glutathione 
• 2575-73-7 Se-benzyl-L-selenocysteine 
• 146552-76-3 Se-(4-methoxybenzyl)-L-selenocysteine 
• 176300-66-6 selenocysteine 
• 1582790-34-8 C₁₀H₁₀O₄SSe 
• 1639843-33-6 bisN-Fmoc-L-selenocystine 

Relevant articles and documents

Selenazolidine: A selenium containing proline surrogate in peptide science

In the search for new peptide ligands containing selenium in their sequences, we investigated l-4-selenazolidine-carboxylic acid (selenazolidine, Sez) as a proline analog with the chalcogen atom in the γ-position of the ring. In contrast to proteinogenic selenocysteine (Sec) and selenomethionine (SeMet), the incorporation within a peptide sequence of such a non-natural amino acid has never been studied. There is thus a great interest in increasing the possibility of selenium insertion within peptides, especially for sequences that do not possess a sulfur containing amino acid (Cys or Met), by offering other selenated residues suitable for peptide synthesis protocols. Herein, we have evaluated selenazolidine in Boc/Bzl and Fmoc/tBu strategies through the synthesis of a model tripeptide, both in solution and on a solid support. Special attention was paid to the stability of the Sez residue in basic conditions. Thus, generic protocols have been optimized to synthesize Sez-containing peptides, through the use of an Fmoc-Xxx-Sez-OH dipeptide unit. As an example, a new analog of the vasopressin receptor-1A antagonist was prepared, in which Pro was replaced with Sez [3-(4-hydroxyphenyl)-propionyl-d-Tyr(Me)-Phe-Gln-Asn-Arg-Sez-Arg-NH2]. Both proline and such pseudo-proline containing peptides exhibited similar pharmacological properties and endopeptidase stabilities indicating that the presence of the selenium atom has minimal functional effects. Taking into account the straightforward handling of Sez as a dipeptide building block in a conventional Fmoc/tBu SPPS strategy, this result suggested a wide range of potential uses of the Sez amino acid in peptide chemistry, for instance as a viable proline surrogate as well as a selenium probe, complementary to Sec and SeMet, for NMR and mass spectrometry analytical purposes.

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Selenium and sulfur in exchange reactions: A comparative study

Cysteamine reduces selenocystamine to form hemiselenocystamine and then cystamine. The rate constants are k1 = 1.3 × 105 M-1 s-1; k-1 = 2.6 × 107 M-1 s-1; k2 = 11 M-1 s-1; and k-2 = 1.4 × 103 M-1 s-1, respectively. Rate constants for reactions of cysteine/selenocystine are similar. Reaction rates of selenium as a nucle'phile and as an electrophile are 2-3 and 4 orders of magnitude higher, respectively, than those of sulfur. Sulfides and selenides are comparable as leaving groups.

Preparation method for L-selenocysteine

The invention belongs to the field of chemical synthesis, and concretely relates to a synthetic method for L-selenocysteine. The method comprises the following steps: a, chloridizing L-serine hydrochloride to obtain 3-chloro-L-alanine hydrochloride; b, performing seleno-reaction of 3-chloro-L-alanine hydrochloride prepared by step a under alkaline condition to obtain L-selenocystine; and c, performing reduction reaction of L-selenocystine to obtain L-selenocysteine. The method has simple steps, high yield, low cost, and good application prospect.