S-adenosylhomocysteine analogues with the carbon-5' and sulfur atoms replaced by a vinyl unit.
Cross-metathesis of suitably protected 5'-deoxy-5'-methyleneadenosines with racemic and chiral N-Boc-protected six-carbon amino acids bearing a terminal double bond in the presence of the Hoveyda-Grubbs catalyst gave adenosylhomocysteine analogues with the C5'-C6' double bond. Bromination with pyridinium tribromide and dehydrobromination with DBU followed by standard deprotections yielded the 5'-(bromo)vinyl analogue. [structure: see text]
Andrei
Daniela
D
Department of Chemistry and Biochemistry, Florida International University, Miami, FL 33199, USA.
Wnuk
Stanislaw F
SF
D000241:Adenosine / Q000031:analogs & derivatives / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D012435:S-Adenosylhomocysteine / Q000737:chemistry*; D013455:Sulfur / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry*
D014753:Vinyl Compounds; D013455:Sulfur; D012435:S-Adenosylhomocysteine; D000241:Adenosine