Borchardt R T, Wu Y S, Wu B S
J Med Chem. 1978 Dec;21(12):1307-10. doi: 10.1021/jm00210a026.
A series of 2',3'-acyclic analogues of S-adenosyl-L-homocysteine were synthesized and evaluated as inhibitors of S-adenosyl-L-methionine-dependent methyltransferases. The 2',3'-acyclic analogues were prepared by periodate oxidation of the corresponding ribonucleosides, followed by reduction of the intermediate dialdehydes with sodium borohydride. These 2',3'-acyclic ribonucleosides were inactive as inhibitors of histamine N-methyltransferase, catechol O-methyltransferase, phenylethanolamine N-methyltransferase, and hydroxyindole O-methyltransferase. These results suggest that the rigidity of the ribosyl ring of S-adenosyl-L-homocysteine is crucial to its enzymatic bindings.
合成了一系列S-腺苷-L-高半胱氨酸的2',3'-无环类似物，并将其作为S-腺苷-L-甲硫氨酸依赖性甲基转移酶的抑制剂进行评估。通过高碘酸盐氧化相应的核糖核苷，然后用硼氢化钠还原中间的二醛来制备2',3'-无环类似物。这些2',3'-无环核糖核苷作为组胺N-甲基转移酶、儿茶酚O-甲基转移酶、苯乙醇胺N-甲基转移酶和羟基吲哚O-甲基转移酶的抑制剂没有活性。这些结果表明，S-腺苷-L-高半胱氨酸核糖基环的刚性对其酶结合至关重要。
