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US 10,590,160 B2Granted
Efficient synthesis of nicotinamide mononucleotide
AssigneeCornell University
InventorsAnthony Sauve, Farheen Sultana Mohammad
Life of this patent
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Abstract
The invention provides a process for the preparation of nicotinamide mononucleotide having formula (I): The method involves the protection of nicotinamide riboside by ketalization, followed by phosphorylation and then deprotection to provide nicotinamide mononucleotide.
Claims9
A process for the preparation of nicotinamide mononucleotide having formula (I):
- or a salt thereof, wherein the process comprises the steps of:
- (i) reacting nicotinamide riboside having formula (II):
- with a ketalization reagent that is R1R2C(OR3)(OR4) or R1R2C═O, wherein R1-R4 are independently C1-C6 alkyl in a solvent in the presence of an acid catalyst, to form a compound of formula (III):
- (ii) isolating the compound of formula (III),
- (iii) reacting the compound of formula (III) with a mixture of POCl3 and PO(OR5)3, wherein R5 is C1-C6 alkyl, followed by treatment with water to form a compound of formula (IV):
- or a salt thereof,
- (iv) isolating the compound of formula (IV),
- (v) reacting the compound of formula (IV) with an acid catalyst in a solvent or mixture of solvents to provide nicotinamide mononucleotide, and
- (vi) isolating nicotinamide mononucleotide.
6 more elements
A process for the preparation of a compound of formula (IV):
- or a salt thereof,
- wherein R1 and R2 are independently C1-C6 alkyl,
- wherein the process comprises the step of reacting a compound of formula (III):
- with a mixture of POCl3 and PO(OR5)3, wherein R5 is C1-C6 alkyl, followed by treatment with water to form a compound of formula (IV).
1 more element
Dependencies are inferred from the claim text.