title: Synthesis of an azide-bearing N-mustard analogue of S-adenosyl-L-methionine.
abstract: The synthesis of an azide-bearing N-mustard S-adenosyl-L-methionine (SAM) analogue, 8-azido-5'-(diaminobutyric acid)-N-iodoethyl-5'-deoxyadenosine, has been accomplished in 10 steps from commercially available 2',3'-isopropylidene adenosine. Critical to this success was executing C8 azidation prior to derivatizing the 5'-position of the ribose sugar and the late stage alkylation of the 5' amino group with bromoethanol, which was necessitated by the reactivity of the aryl azide moiety. The azide-bearing N-mustard is envisioned as a useful biochemical tool by which to probe DNA and protein methylation patterns.
authors: Department of Chemistry, Wake Forest University, Winston-Salem, North Carolina 27109, USA.
authors: Van
authors: V
authors: Mai
authors: Lindsay R
authors: LR
authors: Comstock
mesh_terms: D000478:Alkylation; D001386:Azides / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D004247:DNA / Q000378:metabolism; D000076123:DNA (Cytosine-5-)-Methyltransferase 1; D004248:DNA (Cytosine-5-)-Methyltransferases / Q000378:metabolism; D003839:Deoxyadenosines / Q000737:chemistry; D006801:Humans; D008745:Methylation; D015335:Molecular Probes / Q000138:chemical synthesis*; D009150:Mustard Compounds / Q000737:chemistry; D012266:Ribose / Q000737:chemistry; D012436:S-Adenosylmethionine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*
chemical_list: D001386:Azides; D003839:Deoxyadenosines; D015335:Molecular Probes; D009150:Mustard Compounds; C033714:5'-deoxyadenosine; D012266:Ribose; D012436:S-Adenosylmethionine; D004247:DNA; D000076123:DNA (Cytosine-5-)-Methyltransferase 1; D004248:DNA (Cytosine-5-)-Methyltransferases