(2R,4R)-2-[D-Xylo-tetrahydroxybut-1-yl]-1,3-thiazolidine-4-carboxylic acid
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(2R,4R)-2-[D-Xylo-tetrahydroxybut-1-yl]-1,3-thiazolidine-4-carboxylic acid

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(2R,4R)-2-[D-Xylo-tetrahydroxybut-1-yl]-1,3-thiazolidine-4-carboxylic acid, a remarkable bioactive compound prevalent in the biomedical sector, presents immense promise as a therapeutic intervention for diverse ailments. Uniquely structured, this compound holds immense potential in aiding the targeted modulation of molecular pathways that underlie prevalent conditions such as cancer, diabetes, and inflammation. Within the pharmaceutical realm, its significant involvement in drug development aimed at precise molecular targets is an area of immense interest and inquiry.

Category
Cyclic Amino Acids
Catalog number
BAT-008965
CAS number
110270-19-4
Molecular Formula
C8H15NO6S
Molecular Weight
253.27
(2R,4R)-2-[D-Xylo-tetrahydroxybut-1-yl]-1,3-thiazolidine-4-carboxylic acid
IUPAC Name
(2R,4R)-2-[(1R,2S,3R)-1,2,3,4-tetrahydroxybutyl]-1,3-thiazolidine-4-carboxylic acid
Synonyms
(2R,4R)-2-[D-Xylo-tetrahydroxybutyl]-1,3-thiazolidine-4-carboxylic acid
InChI
InChI=1S/C8H15NO6S/c10-1-4(11)5(12)6(13)7-9-3(2-16-7)8(14)15/h3-7,9-13H,1-2H2,(H,14,15)/t3-,4+,5-,6+,7+/m0/s1
InChI Key
AGZXTDUDXXPCMJ-PJEQPVAWSA-N
Canonical SMILES
C1C(NC(S1)C(C(C(CO)O)O)O)C(=O)O
1.Crystal structures of (2R,4R)-2-(polyhydroxyalkyl)-1,3-thiazolidine-4-carboxylic acids: condensation products of l-cysteine with d-hexoses.
Tarnawski M1, Slepokura K, Lis T. Carbohydr Res. 2011 Jan 3;346(1):127-32. doi: 10.1016/j.carres.2010.10.021. Epub 2010 Oct 30.
We report herein the first crystal structures of (4-carboxy-1,3-thiazolidin-2-yl)pentitols [2-(polyhydroxyalkyl)thiazolidine-4-carboxylic acids], condensation products of l-cysteine with d-galactose and d-mannose: 2-(d-galacto-pentahydroxypentyl)thiazolidine-4-carboxylic acid hydrate, Gal-Cys·H(2)O (1), and 2-(d-manno-pentahydroxypentyl)thiazolidine-4-carboxylic acid hydrate, Man-Cys·H(2)O (2). In 1 and 2 the compounds crystallize as zwitterions, with the carboxylic groups deprotonated and the thiazolidine N atoms protonated. The sugar moiety and carboxylate group are in a cis configuration relative to the thiazolidinium ring, which adopts different conformation: twisted (T) on C(β)-S in 1, and S-puckered envelope (E) in 2. The carbon chain of the galactosyl/mannosyl moiety remains in an extended zig-zag conformation. The orientation of the sugar O2 atom with respect to the thiazolidinium S and N atoms is trans-gauche in 1 and gauche-gauche in 2.
2.Analysis of a model reaction system containing cysteine and (E)-2-methyl-2-butenal, (E)-2-hexenal, or mesityl oxide.
Starkenmann C1. J Agric Food Chem. 2003 Nov 19;51(24):7146-55.
Cysteine conjugates, resulting from the addition of cysteine to alpha,beta-unsaturated carbonyl compounds, are important precursors of odorant sulfur compounds in food flavors. The aim of this work was to better understand this chemistry in the light of the unexpected double addition of cysteine to two unsaturated aldehydes. These reactions were studied as a function of pH. When (E)-2-methyl-2-butenal (tiglic aldehyde, 4) was treated with cysteine in water at pH 8, the major product formed was the new compound (4R)-2-(2-[[(2R)-2-amino-2-carboxyethyl]thio]methylpropyl)-1,3-thiazolidine-4-carboxylic acid (6). Under acidic conditions (pH 1), we also observed a double addition, but the second cysteine was linked by a vinylic sulfide bond to form the previously unreported major product, (2R,2'R,E)-S,S'-(2,3-dimethyl-1-propene-1,3-diyl)bis-cysteine (7). When (E)-2-hexenal (12) was treated with cysteine under acidic conditions, the major product was the novel (4R,2' 'R)-2-[2'-(2' '-amino-2' '-carboxyethylthio)pentyl]-1,3-thiazolidine-4-carboxylic acid (13), and the formation of an vinylic sulfide compound analogous to 7 was not observed.
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