Efficient Synthesis of S-Adenosyl-L-Homocysteine Natural Product Analogues and Their Use to Elucidate the Structural Determinant for Cofactor Binding of the DNA Methyltransferase M·HhaI

✍ Scribed by Marc Pignot; Goran Pljevaljcic; Elmar Weinhold

• Publisher: John Wiley and Sons
• Year: 2000
• Tongue: English
• Weight: 312 KB
• Volume: 2000
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(200002)2000:3<549::aid-ejoc549>3.0.co;2-7

✦ Synopsis

5Ј-Acetylthio-5Ј-deoxy-2Ј,3Ј-O-isopropylideneadenosine (8) was directly prepared from commercially available 2Ј,3Ј-Oisopropylideneadenosine ( 7) and thioacetic acid under Mitsunobu conditions in almost quantitative yield. In situ cleavage of the acetylthio function of 8 followed by coupling with different alkyl bromides proceeded with high yields. Deprotection of the obtained 5Ј-thionucleosides yielded the S-adenosyl-L-homocysteine analogues decarboxylated