Département de Chimie , Université de Montréal , C.P. 6128, Succursale Centre-Ville , Montréal , Québec H3C 3J7 , Canada.
Org Lett. 2018 Oct 5;20(19):6126-6129. doi: 10.1021/acs.orglett.8b02575. Epub 2018 Sep 19.
α- N-(Fmoc)Amino-γ-lactam dipeptides with a variety of β-substituents were synthesized stereoselectively with minimal β-elimination by routes employing, respectively, Mitsunobu chemistry and cyclic sulfamidate nucleophilic ring opening from trans- and cis-β-hydroxy-α-amino-γ-lactam precursors. This diversity-oriented method provides stereochemically pure dipeptide mimics bearing Cys, Ser, Thr, Dap, Dab, His, and other amino acid residues with constrained backbone and side chain conformations.
采用分别采用 Mitsunobu 化学和反式及顺式-β-羟基-α-氨基-γ-内酰胺前体的环状磺酰胺亲核开环反应路线，立体选择性地合成了具有各种β-取代基的α-N-(Fmoc)氨基-γ-内酰胺二肽，β-消除反应最小。这种针对多样性的方法提供了立体化学纯的二肽模拟物，其带有 Cys、Ser、Thr、Dap、Dab、His 和其他具有约束主链和侧链构象的氨基酸残基。
