Dolichol monophosphate mannose

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Dolichol monophosphate mannose
DolicholMPM.svg
Names
IUPAC name
[(6E,10E,14E,18E,22E,26E,30E,34E,38E,42E,46E,50E,54E,58E,62E,66E,70E,74E)- 3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63,67,71,75,79-icosamethyloctaconta-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62,66,70,74,78-nonadecaenyl] [(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl] hydrogen phosphate
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C106H175O9P/c1-82(2)41-22-42-83(3)43-23-44-84(4)45-24-46-85(5)47-25-48-86(6)49-26-50-87(7)51-27-52-88(8)53-28-54-89(9)55-29-56-90(10)57-30-58-91(11)59-31-60-92(12)61-32-62-93(13)63-33-64-94(14)65-34-66-95(15)67-35-68-96(16)69-36-70-97(17)71-37-72-98(18)73-38-74-99(19)75-39-76-100(20)77-40-78-101(21)79-80-113-116(111,112)115-106-105(110)104(109)103(108)102(81-107)114-106/h41,43,45,47,49,51,53,55,57,59,61,63,65,67,69,71,73,75,77,101-110H,22-40,42,44,46,48,50,52,54,56,58,60,62,64,66,68,70,72,74,76,78-81H2,1-21H3,(H,111,112)/b83-43+,84-45+,85-47+,86-49+,87-51+,88-53+,89-55+,90-57+,91-59+,92-61+,93-63+,94-65+,95-67+,96-69+,97-71+,98-73+,99-75+,100-77+/t101?,102-,103-,104+,105+,106+/m1/s1
    Key: IPAOLVGASNLKMS-WIFKHAHXSA-N
  • CC(CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CCC=C(C)C)CCOP(=O)(O)O[C@H]1[C@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
Properties
C106H175O9P
Molar mass 1624.531 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Dolichol monophosphate mannose is a chemical compound involved in glycosylation. [1]

Related Research Articles

A congenital disorder of glycosylation is one of several rare inborn errors of metabolism in which glycosylation of a variety of tissue proteins and/or lipids is deficient or defective. Congenital disorders of glycosylation are sometimes known as CDG syndromes. They often cause serious, sometimes fatal, malfunction of several different organ systems in affected infants. The most common sub-type is PMM2-CDG where the genetic defect leads to the loss of phosphomannomutase 2 (PMM2), the enzyme responsible for the conversion of mannose-6-phosphate into mannose-1-phosphate.

Dolichol refers to any of a group of long-chain mostly unsaturated organic compounds that are made up of varying numbers of isoprene units terminating in an α-saturated isoprenoid group, containing an alcohol functional group.

<span class="mw-page-title-main">Prenol</span> Chemical compound

Prenol, or 3-methyl-2-buten-1-ol, is a natural alcohol. It is one of the most simple terpenoids. It is a clear colorless oil that is reasonably soluble in water and miscible with most common organic solvents. It has a fruity odor and is used occasionally in perfumery.

<span class="mw-page-title-main">Oligosaccharyltransferase</span>

Oligosaccharyltransferase or OST (EC 2.4.1.119) is a membrane protein complex that transfers a 14-sugar oligosaccharide from dolichol to nascent protein. It is a type of glycosyltransferase. The sugar Glc3Man9GlcNAc2 (where Glc=Glucose, Man=Mannose, and GlcNAc=N-acetylglucosamine) is attached to an asparagine (Asn) residue in the sequence Asn-X-Ser or Asn-X-Thr where X is any amino acid except proline. This sequence is called a glycosylation sequon. The reaction catalyzed by OST is the central step in the N-linked glycosylation pathway.

The mannose receptor is a C-type lectin primarily present on the surface of macrophages, immature dendritic cells and liver sinusoidal endothelial cells, but is also expressed on the surface of skin cells such as human dermal fibroblasts and keratinocytes. It is the first member of a family of endocytic receptors that includes Endo180 (CD280), M-type PLA2R, and DEC-205 (CD205).

In enzymology, a chitobiosyldiphosphodolichol beta-mannosyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a dolichyl-phosphate beta-D-mannosyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a dolichyl-phosphate-mannose-protein mannosyltransferase is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">PMM2</span> Protein-coding gene in the species Homo sapiens

Phosphomannomutase 2 is an enzyme that in humans is encoded by the PMM2 gene.

<span class="mw-page-title-main">PMM1</span>

Phosphomannomutase 1 is an enzyme that in humans is encoded by the PMM1 gene.

<span class="mw-page-title-main">DPM1</span> Protein-coding gene in the species Homo sapiens

Dolichol-phosphate mannosyltransferase is an enzyme that in humans is encoded by the DPM1 gene.

<span class="mw-page-title-main">MPDU1</span> Protein-coding gene in the species Homo sapiens

Mannose-P-dolichol utilization defect 1 protein is a protein that in humans is encoded by the MPDU1 gene.

<span class="mw-page-title-main">ALG12</span> Enzyme-coding gene in humans

Dolichyl-P-Man:Man(7)GlcNAc(2)-PP-dolichyl-alpha-1,6-mannosyltransferase is an enzyme that in humans is encoded by the ALG12 gene.

<span class="mw-page-title-main">PIGB</span>

GPI mannosyltransferase 3 is an enzyme that in humans is encoded by the PIGB gene.

<i>N</i>-linked glycosylation

N-linked glycosylation, is the attachment of an oligosaccharide, a carbohydrate consisting of several sugar molecules, sometimes also referred to as glycan, to a nitrogen atom, in a process called N-glycosylation, studied in biochemistry. This type of linkage is important for both the structure and function of many eukaryotic proteins. The N-linked glycosylation process occurs in eukaryotes and widely in archaea, but very rarely in bacteria. The nature of N-linked glycans attached to a glycoprotein is determined by the protein and the cell in which it is expressed. It also varies across species. Different species synthesize different types of N-linked glycan.

<span class="mw-page-title-main">DPM3</span> Protein-coding gene in the species Homo sapiens

dolichyl-phosphate mannosyltransferase polypeptide 3, also known as DPM3, is a human gene.

<span class="mw-page-title-main">DPM2</span> Protein-coding gene in the species Homo sapiens

Dolichol phosphate-mannose biosynthesis regulatory protein is a protein that in humans is encoded by the DPM2 gene.

Dolichyl, related to Dolichol, is used in the names of:

Glypiation is the addition by covalent bonding of a glycosylphosphatidylinositol (GPI) anchor and is a common post-translational modification that localizes proteins to cell membranes. This special kind of glycosylation is widely detected on surface glycoproteins in eukaryotes and some Archaea.

GDP-Man:Man2GlcNAc2-PP-dolichol alpha-1,6-mannosyltransferase is an enzyme with systematic name GDP-D-mannose:D-Man-alpha-(1->3)-D-Man-beta-(1->4)-D-GlcNAc-beta-(1->4)-D-GlcNAc-diphosphodolichol alpha-6-mannosyltransferase. This enzyme catalyses the following chemical reaction

References

  1. ↑ Maeda, Yusuke; Kinoshita, Taroh (2008). "Dolichol-phosphate mannose synthase: Structure, function and regulation". Biochimica et Biophysica Acta (BBA) - General Subjects. 1780 (6): 861–868. doi:10.1016/j.bbagen.2008.03.005. PMID   18387370.


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