title: S-homoadenosyl-L-cysteine and S-homoadenosyl-L-homocysteine. Synthesis and binding studies of hon-hydrolyzed substrate analogues with S-adenosyl-L-homocysteine hydrolase.
abstract: Treatment of homoadenosine [9-(5-deoxy-beta-D-ribo-hexofuranosyl)adenine] with thionyl chloride and pyridine in acetonitrile gave 6'-chloro-6'-deoxyhomoadenosine, which underwent nucleophilic displacement with L-cysteine or L-homocysteine to give homologated analogues of S-adenosyl-L-homocysteine. Each amino acid in aqueous sodium hydroxide at 60 degrees C gave excellent conversion from the chloronucleoside, and adsorption on Amberlite XAD-4 resin provided more convenient isolation than prior methods. Weak binding of these non-hydrolyzed analogues to S-adenosyl-L-homocysteine hydrolase was observed.
authors.affiliation: Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602-5700, USA.
authors.forename: Robert W
authors.initials: RW
authors.lastname: Miles
authors.forename: Lars P C
authors.initials: LP
authors.lastname: Nielsen
authors.forename: Gregory J
authors.initials: GJ
authors.lastname: Ewing
authors.forename: Daniel
authors.initials: D
authors.lastname: Yin
authors.forename: Ronald T
authors.initials: RT
authors.lastname: Borchardt
authors.forename: Morris J
authors.initials: MJ
authors.lastname: Robins
mesh_terms: D043383:Adenosylhomocysteinase; D003545:Cysteine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D006710:Homocysteine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology*; D006801:Humans; D006867:Hydrolases / Q000037:antagonists & inhibitors* / Q000378:metabolism; D007700:Kinetics; D010920:Placenta / Q000201:enzymology; D011485:Protein Binding; D012436:S-Adenosylmethionine / Q000031:analogs & derivatives
chemical_list: D004791:Enzyme Inhibitors; C475802:S-homoadenosyl-L-cysteine; C475803:S-homoadenosyl-L-homocysteine; D006710:Homocysteine; D012436:S-Adenosylmethionine; D006867:Hydrolases; D043383:Adenosylhomocysteinase; D003545:Cysteine