Format

Send to

Choose Destination
Org Lett. 2014 Jun 6;16(11):3056-9. doi: 10.1021/ol501169y. Epub 2014 May 22.

Large-scale, protection-free synthesis of Se-adenosyl-L-selenomethionine analogues and their application as cofactor surrogates of methyltransferases.

Author information

1
Molecular Pharmacology and Chemistry Program and ‡Tri-Institutional Training Program in Chemical Biology, Memorial Sloan Kettering Cancer Center , New York, New York 10065, United States.

Abstract

S-adenosyl-L-methionine (SAM) analogues have previously demonstrated their utility as chemical reporters of methyltransferases. Here we describe the facile, large-scale synthesis of Se-alkyl Se-adenosyl-L-selenomethionine (SeAM) analogues and their precursor, Se-adenosyl-L-selenohomocysteine (SeAH). Comparison of SeAM analogues with their equivalent SAM analogues suggests that sulfonium-to-selenonium substitution can enhance their compatibility with certain protein methyltransferases, favoring otherwise less reactive SAM analogues. Ready access to SeAH therefore enables further application of SeAM analogues as chemical reporters of diverse methyltransferases.

PMID:
24852128
PMCID:
PMC4059250
DOI:
10.1021/ol501169y
[Indexed for MEDLINE]
Free PMC Article

Supplemental Content

Full text links

Icon for American Chemical Society Icon for PubMed Central
Loading ...
Support Center