Synthesis of natural and non natural orthogonally protected lanthionines from N-tritylserine and allo-threonine derivatives
作者:Christophe Dugave、André Ménez
DOI:10.1016/s0957-4166(97)00109-2
日期:1997.5
This strategy was applied to the synthesis of lanthionines, the monosulfide analogs of cystine. Orthogonally protected sulfide adducts from L- and D-cysteines, threo-β-methyl-L-cysteine and D-penicillamine were isolated in 81–88% yield (ee>98%). This strategy was applied to the prepration of lanthionine and cyclolanthionine suitably protected for peptide synthesis.
衍生自亲电子的反应性Ñ -tritylserine,苏氨酸和异基因朝向选择的亲核试剂的苏氨酸酯进行了研究。用N-三苯并碘丙氨酸和软亲核试剂(例如硫醇)可获得替代产品的最佳收率。该策略被用于合成胱氨酸的单硫醚类似物羊毛硫氨酸。从L-和d-半胱氨酸,正交保护的加合物硫化物苏- β -甲基-L-半胱氨酸和d青霉胺在81-88%的产率(ee值> 98%)中分离得到。将该策略应用于适当保护用于肽合成的羊毛硫氨酸和环羊毛硫氨酸的制备。