29621-88-3

Basic information

• Product Name: L-SELENOCYSTINE
• Synonyms: SELENO-L-CYSTINE;(R,R)-3,3'-DISELENO-BIS(2-AMINOPROPIONIC ACID);3,3'-DISELENO-L-ALANINE;L-SELENOCYSTINE;3’-diselenodi-l-alanin;l-3,3’-diselenodialanine;L-SELENOCYSTINE 98%;(R,R)-3,3μ-Diseleno-bis(2-aminopropionic acid), L-Selenocystine
• CAS NO: 29621-88-3
• Molecular Formula: C₆H₁₂N₂O₄Se₂
• Molecular Weight: 334.09
• EINECS: 275-728-7
• Product Categories: amino acids
• Mol File: 29621-88-3.mol
• Article Data: 18

Chemical Properties

• Melting Point: 224.5-229.5 °C(lit.)
• Boiling Point: 538.3°Cat760mmHg
• Flash Point: 279.3°C
• Appearance: Yellow/Powder
• Density: g/cm³
• Storage Temp.: 2-8°C
• PKA: 1.69±0.10(Predicted)
• BRN: 1969559
• CAS DataBase Reference: L-SELENOCYSTINE(CAS DataBase Reference)
• NIST Chemistry Reference: L-SELENOCYSTINE(29621-88-3)
• EPA Substance Registry System: L-SELENOCYSTINE(29621-88-3)

Safety Data

• Hazard Codes: T,N
• Statements: 23/25-33-50/53
• Safety Statements: 20/21-28-45-60-61
• RIDADR: UN 3283 6.1/PG 3
• WGK Germany: 3
• RTECS: AY6032000
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 29621-88-3(Hazardous Substances Data)

Usage

Description

L-Selenocystine is a diselenide-bridged amino acid that may be confused with selenocysteine (Sec), which is a rare amino acid featuring a single selenium atom. L-Selenocystine is a redox-active selenium compound that has both anti- and pro-oxidant actions. This compound can be reduced by low molecular thiols and disulfide reductases to Sec. It is reduced to Sec by mammalian thioredoxin reductase (apparent Km = 6.0 μM), and this property can be used to assay thioredoxin reductase activity. L-Selenocystine induces an unfolded protein response, ER stress, and large cytoplasmic vacuolization in HeLa cells and has cytostatic effects in a range of cancer cell types.

Chemical Properties

yellow fine powder

Uses

Seleno-L-cystine can be used for the synthesis of:Biologically active selenol compounds.Non-natural selenylated diamino acids.

Upstream product

• 109276-78-0 L-dibenzyl N,N'-di(benzyloxycarbonyl)selenocystinate 
• 195324-31-3 dimethyl 3,3'-diselanediyl-(2R,2'R)-bis(2-((tertbutoxycarbonyl)amino)propanoate) 
• 1148111-64-1 C₃H₆NO₂Se^(1-) 
• 2575-73-7 2-amino-3-benzylselanyl-propionic acid 
• 7664-41-7 ammonia 
• 3614-08-2 L-selenocysteine 
• 83-88-5 riboflavin 
• 1242409-39-7 hemiselenocystine 
• 23926-58-1 N,N'-bis(benzyloxycarbonyl)-L-cystine diethyl ester 
• 2731-73-9 2-amino-3-chloropropanoic acid 
• 51887-89-9 β-chloro-L-alanine hydrochloride 
• 739301-12-3 seleno-L-cysteine dimethyl ester 
• 2575-73-7 Se-benzyl-L-selenocysteine 
• 25248-96-8 O-acetyl-D-serine 

Downstream Products

• 2575-73-7 2-amino-3-benzylselanyl-propionic acid 
• 3614-08-2 L-selenocysteine 
• 27025-41-8 Oxidized glutathione 
• 188609-44-1 C₁₃H₂₂N₄O₈SSe 
• 83-88-5 riboflavin 
• 27317-69-7 N-tert-butoxycarbonyl-L-alanyl-L-alanine 
• 1365284-51-0 Fmoc-Sec(Bzl)-OH 
• 1639843-33-6 bisN-Fmoc-L-selenocystine 
• 1582790-34-8 C₁₀H₁₀O₄SSe 
• 176300-66-6 selenocysteine 

Relevant articles and documents

Studies on the reaction between reduced riboflavin and selenocystine

Selenocysteine (Sec) is a crucial component of mammalian thioredoxin reductase (TrxR) where it serves as a nucleophile for disulfide bond rupture in thioredoxin (Trx). Generation of the reduced state of Sec in TrxR requires consecutive two electron transfer steps, namely: (i) from NADPH to flavin adenine dinucleotide, (ii) from reduced flavin to the disulfide bond Cys59-S-S-Cys64, and finally (iii) from Cys59 and Cys64 to the selenosulfide bond Cys497-S-Se-Sec498. In this work, we studied the reaction between reduced riboflavin (RibH2) and selenocystine (Sec-Sec), an oxidized form of Sec. The interaction between RibH2 and Sec-Sec proceeded relatively slowly in comparison with its reverse reaction, that is, reduction of riboflavin (Rib) by Sec. The rate constant for the reaction between RibH2 and Sec-Sec was (7.9?±?0.1)?×?10?2?M?1 s?1 (pH 7.0, 25.0°C). The reaction between Rib and Sec proceeded via two steps, namely, a rapid reversible binding of Rib to Sec having a protonated selenol group to form a Sec-Rib complex, followed by nucleophilic attack of Sec-Rib by a second Sec molecule harboring a deprotonated selenol group. The equilibrium constant for the overall reduction process of Rib by Sec is (1.2?±?0.1)?×?106?M?1 (25.0°C). The finding that the interaction of RibH2 with oxidized selenol is reversible with its equilibrium favored toward the reverse reaction provides an additional explanation for the exceptional mechanism of the mammalian Trx/TrxR system involving transient reduction of a disulfide bond.

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.

Diphosphoric acid compounds, and preparation method and application thereof

The invention discloses compounds disclosed as Formula II. In the Formula II, R is disclosed in the specification, wherein R1 is H, OH or halogen; R2 is disclosed in the specification, n1=0-10, n2=0-10, and n3=0-10; Ar is aryl, arylidene, R99-substituted aryl or R99-substituted arylidene; at least one of R3, R4, R5 and R6 is selenium or sulfur atom, and the rest is carbon or nitrogen atom; and R3, R4, R5 and R6 are connected through a single bond or double bond. As for old patients with osteoporosis, the compounds can keep the osteocyte bone formation and bone destroy at an ideal dynamic balance.