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UDP-rhamnose

CAT: 0804-HY-N10573-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N10573-01Size:1 mg
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Description
UDP-rhamnose is one of the substrates for pectin synthesis in cell wall. UDP-rhamnose can be identified in fungi. UDP-rhamnose is one of the most common sugar donors in plants. UDP-rhamnose synthesis requires recombinant enzymes. UDP-rhamnose can be synthesized from UDP-glucose through the consecutive three-step reaction catalyzed by a single structure enzyme in plants[1][2].
CAS Number
1955-26-6
UNSPSC
12352005
Hazard Statement
H371
Target
Endogenous Metabolite
Type
Natural Products
Related Pathways
Metabolic Enzyme/Protease
Applications
Metabolism-sugar/lipid metabolism
Field of Research
Others
Assay Protocol
https://www.medchemexpress.com/udp-rhamnose.html
Purity
96.47
Solubility
H2O : 250 mg/mL (ultrasonic)
Smiles
O[C@H]1[C@@](N2C(NC(C=C2)=O)=O)([H])O[C@@H]([C@H]1O)COP(OP(O[C@@H]3[C@@H]([C@@H]([C@H]([C@@H](O3)C)O)O)O)(O)=O)(O)=O
Molecular Formula
C15H24N2O16P2
Molecular Weight
550.30
Precautions
H371
References & Citations
[1]Martinez V, et al. Biosynthesis of UDP-4-keto-6-deoxyglucose and UDP-rhamnose in pathogenic fungi Magnaporthe grisea and Botryotinia fuckeliana. J Biol Chem. 2012 Jan 6;287 (2) :879-92.|[2]Jianjun Pei, et al., Construction of a novel UDP-rhamnose regeneration system by a two-enzyme reaction system and application in glycosylation of flavonoid, Biochemical Engineering Journal, Volume 139, 2018, Pages 33-42, ISSN 1369-703X.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, protect from light)
Scientific Category
Natural Products
Clinical Information
No Development Reported
Isoform
Human Endogenous Metabolite

Chemical Information

UDP-rhamnose

UDP-beta-L-rhamnose is a UDP-L-rhamnose in which the rhamnose portion has beta-configuration at its anomeric centre.

CAS Number1955-26-6
PubChem CID192751
IUPAC Name[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl] hydrogen phosphate
Molecular FormulaC15H24N2O16P2
Molecular Weight550.30
XLogP-6.1
Topological Polar Surface Area271
Hydrogen Bond Donor Count8
Hydrogen Bond Acceptor Count16
Rotatable Bond Count8
Heavy Atom Count35
Formal Charge0
Complexity948
SMILES
C[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)OP(=O)(O)OP(=O)(O)OC[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=CC(=O)NC3=O)O)O)O)O)O
InChI
InChI=1S/C15H24N2O16P2/c1-5-8(19)10(21)12(23)14(30-5)32-35(27,28)33-34(25,26)29-4-6-9(20)11(22)13(31-6)17-3-2-7(18)16-15(17)24/h2-3,5-6,8-14,19-23H,4H2,1H3,(H,25,26)(H,27,28)(H,16,18,24)/t5-,6+,8-,9+,10+,11+,12+,13+,14+/m0/s1
InChIKey
DRDCJEIZVLVWNC-SLBWPEPYSA-N
Chemical Structure
2D Structure
2D structure of UDP-rhamnose
CAS: 1955-26-6
CID: 192751
Formula: C15H24N2O16P2
MW: 550.30
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight550.30
XLogP3-6.1
Hydrogen Bond Donor Count8
Hydrogen Bond Acceptor Count16
Rotatable Bond Count8
Exact Mass550.06010668
Monoisotopic Mass550.06010668
Topological Polar Surface Area271 Ų
Heavy Atom Count35
Formal Charge0
Complexity948
Isotope Atom Count0
Defined Atom Stereocenter Count9
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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