Karoyan P, Sagan S, Clodic G, Lavielle S, Chassaing G
Laboratoire de Chimie Organique Biologique associé au CNRS, Université P. et M. Curie, UMR 7613, Paris, France.
Bioorg Med Chem Lett. 1998 Jun 2;8(11):1369-74. doi: 10.1016/s0960-894x(98)00219-4.
The asymmetric synthesis of (S)-Boc-N-methyl-p-benzoyl-phenylalanine was performed by alkylation of sultam Boc-sarcosinate. The levorotatory sultam led to (S)-Boc-N-methyl amino acids with high optical purity. This photoreactive amino acid was incorporated into the sequence of a Substance P peptide antagonist. Comparison of the affinity and antagonistic properties of Biotinyl-apa-[D-Pro9, MePhe(pBz)10, Trp11]SP for human tachykinin NK-1 receptor demonstrated that this photoreactive antagonist should be a suitable tool for photolabelling studies.
通过氮杂环丁烷 Boc-肌氨酸酯的烷基化反应实现了 (S)-Boc-N-甲基-对苯甲酰基苯丙氨酸的不对称合成。左旋氮杂环丁烷生成了具有高光学纯度的 (S)-Boc-N-甲基氨基酸。这种光反应性氨基酸被并入 P 物质肽拮抗剂序列中。生物素化的 apa-[D-脯氨酸9，对甲基苯甲酰基苯丙氨酸10，色氨酸11]P 物质对人速激肽 NK-1 受体的亲和力和拮抗特性比较表明，这种光反应性拮抗剂应是光标记研究的合适工具。
