5′-UMP
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5′-UMP
structure -
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CAS No:
58-97-9
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Formula:
C9H13N2O9P
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Chemical Name:
5′-UMP
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Synonyms:
5′-Uridylic acid;Uridylic acid;UMP;5′-UMP;Uridine 5′-monophosphate;Uridine monophosphate;Uridine 5′-phosphate;Uridine 5′-phosphoric acid;Uridine,mono(dihydrogen phosphate) (ester);Uridine,5′-(dihydrogen phosphate);Uridine phosphate;Uridine 5′-(dihydrogen phosphate);UMP (nucleic acid);53624-79-6;81795-92-8
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CAS No:
Description
Uridine 5'-monophosphate (5'-Uridylic acid), a monophosphate form of UTP, can be acquired either from a de novo pathway or degradation products of nucleotides and nucleic acids in vivo and is a major nucleotide analogue in mammalian milk[1].
Solid
Uridine 5'-monophosphate is a pyrimidine ribonucleoside 5'-monophosphate having uracil as the nucleobase. It has a role as a human metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a uridine 5'-phosphate and a pyrimidine ribonucleoside 5'-monophosphate. It is a conjugate acid of a uridine 5'-monophosphate(2-).|5'-Uridylic acid. A uracil nucleotide containing one phosphate group esterified to the sugar moiety in the 2', 3' or 5' position.
Characteristics
166
-3.6
Solid
2.2±0.1 g/cm3
202 °C (decomp)
377.2±35.7 °C
1.754
H2O: soluble50mg/mL, clear, colorless
−20°C
171.8 Ų [M+Na]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]|169.81 Ų [M+H]+ [CCS Type: DT, Method: stepped-field]|175.14 Ų [M+Na]+ [CCS Type: DT, Method: stepped-field]|163.88 Ų [M-H]- [CCS Type: DT, Method: stepped-field]|168 Ų [M+Na]+ [CCS Type: TW, Method: calibrated with polyalanine]|165.7 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|172.3 Ų [M+Na]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|161.2 Ų [M-H]- [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|163.6 Ų [M+Na-2H]- [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|164.1 Ų [M-2H+Na]-
5′-UMP Use and Manufacturing
General procedure: 15mM solutions of selected activated nucleotides, ImpN (N = A, U, C, G, dA)The mixture containing compound 7 (16.3 mg, 44.0 μmol) was co-evaporated with pyridine (3 × 1.0 mL) and dissolved in pyridine (1.0 mL). The solution was added to UMP-morpholidate (43.5 mg, 63.4 μmol), which evaporated with pyiridine (3 × 1.0 mL), in the reaction flask. Moreover, 1H-tetrazole (9.9 mg, 142 μmol) was co-evaporated with pyridine (3 × 1.0 mL) and dissolved in pyridine (300 μL). The solution was transferred to the reaction flask by a syringe and the mixture was then stirred at room temperature for 48 h. The mixture was evaporated and the residue was purified by silica gel chromatography with 7:1 (v/v/v) acetonitrile:water. The absorbance of each fraction was measured at 262 nm and the combined fractions were evaporated. The residue was purified by silica gel chromatography with 7:3:1 (v/v/v) ethyl acetate:methanol:water to give 9 (7.2 mg, 31percent) as a syrup: RThe mixture containing compound 8 (21.8 mg, 58.9 μmol) was co-evaporated with pyridine (3 × 1.0 mL) and dissolved in pyridine (1.0 mL). The solution was added to UMP-morpholidate (80.9 mg, 118 μmol) which evaporated with pyiridine (3 × 1.0 mL) in the reaction flask. Moreover, 1H-tetrazole (15.7 mg, 224 μmol) was co-evaporated with pyridine (3 × 1.0 mL) and dissolved in pyridine (300 μL), then the solution was transferred to the reaction flask by a syringe. The mixture was stirred at room temperature for 48 h. The mixture was evaporated and the residue was purified by silica gel chromatography with 7:1 (v/v/v) acetonitrile:water. The absorbance of each fraction was measured at 262 nm and the combined fractions were evaporated. The residue was purified by silica gel chromatography with 7:3:1 (v/v/v) ethyl acetate:methanol:water to give 10 (19.7 mg, 50percent) as a syrup: R
Used as an intermediate for nucleic acid drugs, health foods and biochemical reagents, and for the manufacture of uridine triphosphate, polyadenylation, fluoroiron and other drugs
5'-Uridylic acid: INACTIVE
Computed Properties
Molecular Weight:324.18
XLogP3:-3.6
Hydrogen Bond Donor Count:5
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:4
Exact Mass:324.03586699
Monoisotopic Mass:324.03586699
Topological Polar Surface Area:166
Heavy Atom Count:21
Complexity:517
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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