Dolichyl phosphate D-mannose
IUPAC 名称
{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid
描述
Dolichyl phosphate D-mannose (DPM) is an intermediate in the biosynthesis of N-glycans. It is a substrate for dolichol-phosphate mannosyltransferase (PMID: 10835346). Dolichol-phosphate mannosyltransferase is a heterotrimeric protein embedded in the endoplasmic reticulum membrane. The first subunit of the heterotrimer appears to be the actual catalyst, and the other two subunits appear to stabilize it. More specifically, dolichol-phosphate-mannose is the donor of mannose groups in the synthesis of the dolichol pyrophosphate-linked precursor oligosaccharide in asparagine-linked glycosylation, in the synthesis of glycosyl phosphatidylinositol (GPI) anchor precursors, in protein O-mannosylation and in protein C-mannosylation. Its synthesis proceeds in two steps. First, cytosolic GDP-mannose reacts with dolichol phosphate exposed on the cytosolic face of the endoplasmic reticulum membrane to form DPM with its mannose moiety oriented toward the cytosol. The DPM molecule then flips in the endoplasmic reticulum membrane, so that its mannose moiety is in the endoplasmic reticulum lumen, accessible to the enzymes that catalyze its transfer to growing glycolipids and glycoproteins. (PMID: 11102867). Dolichyl phosphate D-mannose is also a substrate for protein O-mannosyl-transferase 2 and protein O-mannosyl-transferase 1. [HMDB]
异构
OC[C@H]1O[C@@H](OP(O)(O)=O)[C@@H](O)[C@@H](O)[C@@H]1O
InChI标识符
InChI=1S/C6H13O9P/c7-1-2-3(8)4(9)5(10)6(14-2)15-16(11,12)13/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5+,6+/m1/s1
键
HXXFSFRBOHSIMQ-PQMKYFCFSA-N