beta-D-mannosyldiacetylchitobiosyldiphosphodolichol (YMDB00935)

Identification
YMDB IDYMDB00935
Namebeta-D-mannosyldiacetylchitobiosyldiphosphodolichol
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Descriptionbeta-D-Mannosyldiacetylchitobiosyldiphosphodolichol is involved in dolichyl-diphosphooligosaccharide biosynthesis (N-linked glycosylation) pathway. N-linked glycosylation is an important process found in eukaryotes and archaea, and very rarely in bacteria. During this process certain oligosaccharides are attached to an asparagine residue in the polypeptide chain of the target protein. [Biocyc MANNOSYL-CHITO-DOLICHOL-BIOSYNTHESIS]
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • b-(1->4)-D-mannosylchitobiosyldiphosphodolichol
  • b-1,4-D-mannosylchitobiosyldiphosphodolichol
  • Beta-(1->4)-D-mannosylchitobiosyldiphosphodolichol
  • Beta-(1->4)-delta-mannosylchitobiosyldiphosphodolichol
  • beta-1,4-D-Mannosylchitobiosyldiphosphodolichol
  • beta-1,4-delta-mannosylchitobiosyldiphosphodolichol
  • beta-D-Mannosyldiacetylchitobiosyldiphosphodolichol
  • Beta-delta-mannosyldiacetylchitobiosyldiphosphodolichol
  • Man-beta1->4GlcNAc-beta1->4GlcNAc-PP-Dol
  • b-D-Mannosyldiacetylchitobiosyldiphosphodolichol
  • Β-D-mannosyldiacetylchitobiosyldiphosphodolichol
CAS numberNot Available
WeightAverage: 2110.857
Monoisotopic: 2109.422449182
InChI KeyDIUBVDNAHFKZAP-CZRFIVDBSA-N
InChIInChI=1S/C122H202N2O22P2/c1-86(2)43-24-44-87(3)45-25-46-88(4)47-26-48-89(5)49-27-50-90(6)51-28-52-91(7)53-29-54-92(8)55-30-56-93(9)57-31-58-94(10)59-32-60-95(11)61-33-62-96(12)63-34-64-97(13)65-35-66-98(14)67-36-68-99(15)69-37-70-100(16)71-38-72-101(17)73-39-74-102(18)75-40-76-103(19)77-41-78-104(20)79-42-80-105(21)81-82-139-147(135,136)146-148(137,138)145-121-112(124-107(23)129)115(132)118(110(85-127)142-121)143-120-111(123-106(22)128)114(131)119(109(84-126)141-120)144-122-117(134)116(133)113(130)108(83-125)140-122/h43,45,47,49,51,53,55,57,59,61,63,65,67,69,71,73,75,77,79,105,108-122,125-127,130-134H,24-42,44,46,48,50,52,54,56,58,60,62,64,66,68,70,72,74,76,78,80-85H2,1-23H3,(H,123,128)(H,124,129)(H,135,136)(H,137,138)/b87-45+,88-47+,89-49+,90-51+,91-53-,92-55+,93-57+,94-59+,95-61+,96-63+,97-65+,98-67+,99-69+,100-71-,101-73+,102-75+,103-77+,104-79+/t105?,108-,109-,110-,111-,112-,113-,114-,115-,116+,117+,118-,119-,120+,121-,122+/m1/s1
IUPAC Name{[(2R,3R,4R,5S,6R)-3-acetamido-5-{[(2S,3R,4R,5S,6R)-3-acetamido-4-hydroxy-6-(hydroxymethyl)-5-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}({[hydroxy({[(6E,10E,14E,18E,22Z,26E,30E,34E,38E,42E,46E,50E,54E,58Z,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-nonadecaen-1-yl]oxy})phosphoryl]oxy})phosphinic acid
Traditional IUPAC Name[(2R,3R,4R,5S,6R)-3-acetamido-5-{[(2S,3R,4R,5S,6R)-3-acetamido-4-hydroxy-6-(hydroxymethyl)-5-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy({hydroxy[(6E,10E,14E,18E,22Z,26E,30E,34E,38E,42E,46E,50E,54E,58Z,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-nonadecaen-1-yl]oxyphosphoryl}oxy)phosphinic acid
Chemical FormulaC122H202N2O22P2
SMILESOC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](NC(C)=O)[C@@H](O[C@@H]2CO)O[C@H]2[C@H](O)[C@@H](NC(=O)C)[C@H](O[C@@H]2CO)OP(=O)(O)OP(=O)(O)OCCC(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)CC\C=C(/C)CCC=C(C)C)[C@@H](O)[C@@H](O)[C@@H]1O
Chemical Taxonomy
Description belongs to the class of organic compounds known as polyprenols. These are prenols with more than 4 consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassPolyprenols
Direct ParentPolyprenols
Alternative Parents
Substituents
  • Polyterpenoid
  • Dolichol
  • Polyprenol skeleton
  • Fatty alcohol
  • Fatty acyl
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.0007 g/LALOGPS
logP8.07ALOGPS
logP25.93ChemAxon
logS-6.5ALOGPS
pKa (Strongest Acidic)1.74ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area368.48 ŲChemAxon
Rotatable Bond Count74ChemAxon
Refractivity619.85 m³·mol⁻¹ChemAxon
Polarizability251.76 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm, Golgi
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot AvailableJSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Romero, P. A., Lussier, M., Sdicu, A. M., Bussey, H., Herscovics, A. (1997). "Ktr1p is an alpha-1,2-mannosyltransferase of Saccharomyces cerevisiae. Comparison of the enzymic properties of soluble recombinant Ktr1p and Kre2p/Mnt1p produced in Pichia pastoris." Biochem J 321 ( Pt 2):289-295.9020857
  • Huh, W. K., Falvo, J. V., Gerke, L. C., Carroll, A. S., Howson, R. W., Weissman, J. S., O'Shea, E. K. (2003). "Global analysis of protein localization in budding yeast." Nature 425:686-691.14562095
  • Lobsanov, Y. D., Romero, P. A., Sleno, B., Yu, B., Yip, P., Herscovics, A., Howell, P. L. (2004). "Structure of Kre2p/Mnt1p: a yeast alpha1,2-mannosyltransferase involved in mannoprotein biosynthesis." J Biol Chem 279:17921-17931.14752117
  • Lussier, M., Sdicu, A. M., Camirand, A., Bussey, H. (1996). "Functional characterization of the YUR1, KTR1, and KTR2 genes as members of the yeast KRE2/MNT1 mannosyltransferase gene family." J Biol Chem 271:11001-11008.8631921
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID18396
HMDB IDHMDB11673
Pubchem Compound ID24892765
Kegg IDC05860
ChemSpider IDNot Available
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDD-GALACTOSYL-14-D-GALACTOSYL-14-D-

Enzymes

Protein Details
1. Chitobiosyldiphosphodolichol beta-mannosyltransferase
General function:
Involved in biosynthetic process
Specific function:
Participates in the formation of the lipid-linked precursor oligosaccharide for N-glycosylation. Involved in assembling the dolichol-pyrophosphate-GlcNAc(2)-Man(5) intermediate on the cytoplasmic surface of the ER
Gene Name:
ALG1
Uniprot ID:
P16661
Molecular weight:
51928.5
Reactions
GDP-mannose + chitobiosyldiphosphodolichol → GDP + beta-1,4-D-mannosylchitobiosyldiphosphodolichol.
Protein Details
2. Glycolipid 2-alpha-mannosyltransferase
General function:
Involved in mannosyltransferase activity
Specific function:
Required for the attachment of the third mannose residue of O-linked saccharides
Gene Name:
KRE2
Uniprot ID:
P27809
Molecular weight:
51386.19922
Reactions
Protein Details
3. Alpha-1,2 mannosyltransferase KTR1
General function:
Involved in mannosyltransferase activity
Specific function:
Mannosyltransferase that transfers a mannose residue from GDP-mannose to a range of acceptors in vitro
Gene Name:
KTR1
Uniprot ID:
P27810
Molecular weight:
46021.69922
Reactions
Protein Details
4. Probable mannosyltransferase KTR2
General function:
Involved in mannosyltransferase activity
Specific function:
Involved in N-linked glycosylation
Gene Name:
KTR2
Uniprot ID:
P33550
Molecular weight:
50650.89844
Reactions
Protein Details
5. Probable mannosyltransferase KTR3
General function:
Involved in mannosyltransferase activity
Specific function:
Possible glycosyltransferase
Gene Name:
KTR3
Uniprot ID:
P38130
Molecular weight:
47482.0
Reactions
Protein Details
6. Probable mannosyltransferase YUR1
General function:
Involved in mannosyltransferase activity
Specific function:
Possible glycosyltransferase involved in N-linked glycosylation
Gene Name:
YUR1
Uniprot ID:
P26725
Molecular weight:
50835.60156
Reactions