Adenosine Monophosphate → 6-Chloropurine riboside-5'-O-monophosphate sodium salt

Participants

Reaction Steps

N6-(ω-amino-linker) adenosine 5′-monophosphate can be prepared by contacting 6-chloropurine riboside first with POCl3 then water to produce 6-chloropurine riboside 5′-monophosphate. This intermediate can be reacted with a diamine to produce an N6-(ω-amino-linker) adenosine 5′-monophosphate. Diamines include ethylenediamine (EDA), 1,4-butanediamine (BDA), 1,6-hexanediamine (HDA), 2,2′-oxydiethylamine (ODEA), 2,2′-(ethylenedioxy)diethylamine (EDODEA), and 4,7,10-trioxa-1,13-tridecanediamine (TOTDDA). These diamines provide linkers of (CH2)2, (CH2)4, (CH2)6, C2H4OC2H4 and C3H6OC2H4OC2H4OC3H6, respectively. Additional diamines (and polyamines) such as spermidine (NH2(CH2)3NH(CH2)4NH2), spermine, (NH2(CH2)3NH(CH2)4NH(CH2)3NH2), polyethylene glycol diamines (H2N-PEG-NH2), 1,4-bis(3-aminopropoxy)butane (H2N(CH2)3O (CH2)4O(CH2)3NH2), bis(3-aminopropyl)amine(H2N(CH2)3NH(CH2)3NH2), tris(2-aminoethyl)amine(N(CH2CH2NH2)3), 1,8-diaminooctane (H2N(CH2)8NH2), 1,10-diaminodecane (H2N(CH2)10NH2), and 1,12-diaminododecane (H2N(CH2)12NH2), can also be used.

Provenance & Evidence