S-methyl-5'-thioadenosine
IUPAC 名称
(2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[(methylsulfanyl)methyl]oxolane-3,4-diol
描述
5'-deoxy-5'-methylthioadenosine, also known as S-methyl-5'-thioadenosine or mta, is a member of the class of compounds known as 5'-deoxy-5'-thionucleosides. 5'-deoxy-5'-thionucleosides are 5'-deoxyribonucleosides in which the ribose is thio-substituted at the 5'position by a S-alkyl group. 5'-deoxy-5'-methylthioadenosine is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 5'-deoxy-5'-methylthioadenosine can be found in a number of food items such as allspice, sesame, roselle, and bayberry, which makes 5'-deoxy-5'-methylthioadenosine a potential biomarker for the consumption of these food products. 5'-deoxy-5'-methylthioadenosine can be found primarily in blood and urine, as well as in human fibroblasts, platelet and prostate tissues. 5'-deoxy-5'-methylthioadenosine exists in all living species, ranging from bacteria to humans. In humans, 5'-deoxy-5'-methylthioadenosine is involved in a couple of metabolic pathways, which include methionine metabolism and spermidine and spermine biosynthesis. 5'-deoxy-5'-methylthioadenosine is also involved in several metabolic disorders, some of which include glycine n-methyltransferase deficiency, methionine adenosyltransferase deficiency, homocystinuria-megaloblastic anemia due to defect in cobalamin metabolism, cblg complementation type, and hypermethioninemia.
异构
CSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N
InChI标识符
InChI=1S/C11H15N5O3S/c1-20-2-5-7(17)8(18)11(19-5)16-4-15-6-9(12)13-3-14-10(6)16/h3-5,7-8,11,17-18H,2H2,1H3,(H2,12,13,14)/t5-,7-,8-,11-/m1/s1
键
WUUGFSXJNOTRMR-IOSLPCCCSA-N