176300-66-6

Basic information

• Product Name: (S)-2-aMino-3-hydroselenopropanoic acid
• Synonyms: (S)-2-aMino-3-hydroselenopropanoic acid;D-Selenocysteine;Seleno-D-cysteine
• CAS NO: 176300-66-6
• Molecular Formula: C3H7NO2Se
• Molecular Weight: 168.05318
• EINECS: -0
• Product Categories: Seleno Amino Acid
• Mol File: 176300-66-6.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 440.2±45.0 °C(Predicted)
• Appearance: /
• PKA: 2.16±0.10(Predicted)
• CAS DataBase Reference: (S)-2-aMino-3-hydroselenopropanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-aMino-3-hydroselenopropanoic acid(176300-66-6)
• EPA Substance Registry System: (S)-2-aMino-3-hydroselenopropanoic acid(176300-66-6)

Safety Data

• Hazardous Substances Data: 176300-66-6(Hazardous Substances Data)

Usage

Description

(S)-2-amino-3-hydroselenopropanoic acid is a chemical compound derived from the amino acid cysteine, featuring an amino group and a selenol group in its structure. (S)-2-aMino-3-hydroselenopropanoic acid is unique due to the presence of a selenium atom that replaces the sulfur atom, which is typically found in cysteine. It is recognized for its potential antioxidant properties and its ability to neutralize reactive oxygen species within the body. Furthermore, (S)-2-amino-3-hydroselenopropanoic acid has been investigated for its possible protective role against oxidative damage to cells and its capacity to reduce inflammation. Ongoing research is exploring the therapeutic potential of this compound in various health conditions, particularly those associated with oxidative stress and inflammation.

Uses

Used in Pharmaceutical Industry:
(S)-2-amino-3-hydroselenopropanoic acid is used as a potential therapeutic agent for conditions related to oxidative stress and inflammation. Its antioxidant properties and ability to scavenge reactive oxygen species make it a promising candidate for the development of treatments aimed at reducing cellular damage and inflammation.
Used in Nutritional Supplements:
(S)-2-amino-3-hydroselenopropanoic acid is used as an ingredient in nutritional supplements designed to support overall health and well-being. Its potential antioxidant and anti-inflammatory effects may contribute to the maintenance of a healthy immune system and the reduction of oxidative stress in the body.
Used in Research and Development:
(S)-2-amino-3-hydroselenopropanoic acid is utilized in research and development for the exploration of its therapeutic potential in various health conditions. Scientists are investigating its ability to protect cells from oxidative damage and reduce inflammation, which could lead to the development of new treatments for a range of diseases and disorders.

Upstream product

• 1464-43-3 seleno-L-cystine 
• 97801-57-5 selenodjenkolic acid 
• 13345-95-4 1,5-dihydro-riboflavin 
• 1464-43-3 (2S,2′S)-3,3′-diselanediylbis(2-aminopropanoic acid) 

Downstream Products

• 13345-95-4 1,5-dihydro-riboflavin 
• 1464-43-3 seleno-L-cystine 

Relevant articles and documents

A selenium analogue of firefly D-luciferin with red-shifted bioluminescence emission

A selenium analogue of amino-D-luciferin, aminoseleno-D-luciferin, is synthesized and shown to be a competent substrate for the firefly luciferase enzyme. It has a red-shifted bioluminescence emission maximum at 600 nm (see scheme) and is suitable for bioluminescence imaging studies in living subjects. Copyright

Generation of Recombinant Mammalian Selenoproteins through Genetic Code Expansion with Photocaged Selenocysteine

Selenoproteins contain the amino acid selenocysteine (Sec) and are found in all domains of life. The functions of many selenoproteins are poorly understood, partly due to difficulties in producing recombinant selenoproteins for cell-biological evaluation. Endogenous mammalian selenoproteins are produced through a noncanonical translation mechanism requiring suppression of the UGA stop codon and a Sec insertion sequence (SECIS) element in the 3′ untranslated region of the mRNA. Here, recombinant selenoproteins are generated in mammalian cells through genetic code expansion, circumventing the requirement for the SECIS element and selenium availability. An engineered orthogonal E. coli leucyl-tRNA synthetase/tRNA pair is used to incorporate a photocaged Sec (DMNB-Sec) at the UAG amber stop codon. DMNB-Sec is successfully incorporated into GFP and uncaged by irradiation of living cells. Furthermore, DMNB-Sec is used to generate the native selenoprotein methionine-R-sulfoxide reductase B1 (MsrB1). Importantly, MsrB1 is shown to be catalytically active after uncaging, constituting the first use of genetic code expansion to generate a functional selenoprotein in mammalian systems. The ability to site-specifically introduce Sec directly in mammalian cells, and temporally modulate selenoprotein activity, will aid in the characterization of mammalian selenoprotein function.

Dehalogenation of Halogenated Nucleobases and Nucleosides by Organoselenium Compounds

Halogenated nucleosides, such as 5-iodo-2′-deoxyuridine and 5-iodo-2′-deoxycytidine, are incorporated into the DNA of replicating cells to facilitate DNA single-strand breaks and intra- or interstrand crosslinks upon UV irradiation. In this work, it is shown that the naphthyl-based organoselenium compounds can mediate the dehalogenation of halogenated pyrimidine-based nucleosides, such as 5-X-2′-deoxyuridine and 5-X-2′-deoxycytidine (X=Br or I). The rate of deiodination was found to be significantly higher than that of the debromination for both nucleosides. Furthermore, the deiodination of iodo-cytidines was found to be faster than that of iodo-uridines. The initial rates of the deiodinations of 5-iodocytosine and 5-iodouracil indicated that the nature of the sugar moiety influences the kinetics of the deiodination. For both the nucleobases and nucleosides, the deiodination and debromination reactions follow a halogen-bond-mediated and addition/elimination pathway, respectively.