Peptide Research Laboratory, Department of Studies in Chemistry, Central College Campus, Bangalore University, Dr. B. R. Ambedkar Veedhi, Bangalore 560001, India.
J Org Chem. 2012 Mar 16;77(6):2689-702. doi: 10.1021/jo2024703. Epub 2012 Mar 7.
Synthesis of selenoxo peptides by the treatment of N(α)-protected peptide esters with a combination of PCl(5) and LiAlHSeH is delineated. The method is simple, high-yielding, and free from racemization. Thus obtained selenoxo peptides are used as units for N-terminal chain extension through N(α)-deprotection/coupling to yield peptide-selenoxo peptide hybrids. Multiple selenation is demonstrated by conversion of two peptide bonds of tripeptides into selenoxo peptide bonds. Amino acid derived arylamides are also converted into aryl selenoamides. C(6)H(5)-CSeNH-Val-OMe 8f is obtained as single crystal, and its structure was determined through X-ray diffraction study.
通过 PCl(5) 和 LiAlHSeH 的组合处理 N(α)-保护的肽酯，合成了硒代肽。该方法简单、产率高，且无外消旋化。所得到的硒代肽可作为通过 N(α)-脱保护/偶联进行 N-末端链延伸的单元，以生成肽-硒代肽杂合体。通过将三肽的两个肽键转化为硒代肽键，实现了多硒代。氨基酸衍生的芳酰胺也被转化为芳基硒代酰胺。C(6)H(5)-CSeNH-Val-OMe 8f 作为单晶获得，并通过 X 射线衍射研究确定了其结构。
