Patent ID: 9376461
Filing Date: 2016-06-28
CPC Classification: C07H

Claim Text:
1. A method of non-enzymatic synthesis of compound (III), a 2′-O— or 3′-O-carboxylic ester of the ribose moiety of adenosine-5′-diphosphate ribose (ADP-ribose) or a 2′-O— or 3 ‘-O-carboxylic ester of the ribose moiety of a non-adenosine nucleoside-5’-diphosphate ribose (NDP-ribose) analog, comprising reacting compound (I) defined as (i) nicotinamide adenine dinucleotide (NAD) or a non-adenosine nucleoside-5′-diphosphate ribose (NDP-ribose) analog (I) wherein the non-adenosine substituent moiety is selected from the group consisting of 5′-guanosinyl, 5′-(5-methyluridinyl), 5′-uridinyl, and 5′-cytidinyl; and (ii) the variable LG (leaving group) is selected from the group consisting of a 1-nicotinamidinyl moiety, a 1-nicotinic acid-derived moiety and a halide ion; with a carboxylate ion (II) to produce a mixture of the two O-acylated compounds (III a) and (III b) wherein one of R 1 and R 2 is H, and the other is —C(O)—R x such that the product (III) comprises a mixture of 2′-O-carboxyl-ADP/NDP-ribose (III a, wherein R 1 is H and R 2 is —C(O)—R x ) and 3′-O-carboxyl-ADP/NDP-ribose (III b, wherein R 1 is —C(O)—R x and R 2 is H), wherein R x is an optionally substituted C 1 -C 12 straight or branched alkyl or alkenyl moiety, or an optionally substituted carbocyclyl moiety that is saturated, unsaturated, or aromatic 5-7 membered monocyclic ring or 8-12 membered bicyclic ring, or an optionally substituted heterocyclyl moiety that is a saturated, unsaturated, or aromatic 5-7 membered monocyclic ring or 8-12 membered bicyclic rings comprising one or more heteroatoms selected from N,O, and S.