Acyl phosphate esters and modification of proteins therewith

C - Chemistry – Metallurgy – 07 – F

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C07F 9/09 (2006.01) C07K 14/805 (2006.01)

Patent

CA 2078141

A process for the preparation of acyl phosphate esters of formula (I) or salts thereof, wherein R and R1 are the same or different and represent a linear or branched alkyl group having up to 4 carbon atoms, phenyl or benzyl; n is an integer; when n is 1, R2 represents the group (.alpha.) wherein R4 is a linear or branched alkyl, alkenyl or alkynyl a cyclic alkyl, a cyclic alkenyl, or aryl which may be substituted by alkyl, alkenyl, alkynyl, aryl, arlalkyl, or arylalkenyl or when n is at least 2, R2 represents the group (.beta.) wherein R4 is as defined above; which comprises (a) reacting a compound of formula (II) or a salt thereof, wherein R and R1 are as defined above and R3 is a counter ion, (i) with a compound of formula (III), wherein R4 is as defined above and R5 is a leaving group which is generally known for esterification reactions, in the presence of an ether solvent, when a compound of formula (I) is required or, (ii) with a stoichiometric amount of a compound of formula (IV), wherein n is at least 2, and R4 and R5 are as defined above, in the presence of an ether solvent, when a compound of formu- la (I) wherein n is at least 2 is required, and (b) if required, the acyl phosphate esters of formula (1) so obtained are convert- ed into salts thereof. Novel compounds of formula (I) wherein n is at least 2, and modified proteins obtained using the nov- el compounds are also provided.

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