羟基磺酸、氨基磺酸和磺酰肽的合成

Synthesis of Hydroxyalkanesulfonic Acids, Aminoalkanesulfonic Acids and Sulfonopeptides

具有四面体结构的磺酸衍生物可用于模拟酯键和酰胺键水解的过渡态 ,特别是含有四面体结构磺酰胺键的磺酰肽作为天然肽的硫类似物 ,广泛用于作为酶抑制剂以及用来诱导抗体酶的半抗原 .综述了羟基磺酸、氨基磺酸和磺酰肽的合成 .重点介绍了消旋的和手性的α 和 β 取代的 β 氨基磺酸及其酰氯和亚磺酰氯 ,γ 氨基 α ,β 不饱和磺酸及其酰氯的合成 ,以及由它们作为基元分子通过液相和固相方法来合成α 和 β 取代的 β 磺酰肽、亚磺酰肽及乙烯磺酰肽 .

Sulfonic acid derivatives possessing tetrahedral structure can be used to mimic transition- state analogues of hydrolysis in the ester and amide bonds. Especially sulfonopeptides containing a tetrahedral sulfonamide moiety, as sulfur ananlogues of peptides, were widely used as enzyme inhibitors and heptans for inducing catalytic antibodies. Synthesis of hydroxyalkanesulfonic acids, aminoalkanesulfonic acids and sulfonopeptides is reviewed in this paper, with an emphasis on the synthesis of racemic and chiral alpha- and beta-substituted beta-aminoalkanesulfonic acids, their sulfonyl chlorides, corresponding sulfinyl chlorides, and gamma-amino-alpha, beta-unsaturated alkanesulfonic acids and their sulfonyl chlorides, and their utility as building blocks in solution and solid phase preparations of alpha- and beta-substituted, beta-sulfonopeptide, beta-sulfinopeptide, and vinylogous sulfonamido peptide.