• 我要登录|
  • 免费注册
    |
  • 我的丁香通
    • 企业机构:
    • 成为企业机构
    • 个人用户:
    • 个人中心
  • 移动端
    移动端
丁香通 logo丁香实验_LOGO
搜实验

    大家都在搜

      大家都在搜

        0 人通过求购买到了急需的产品
        免费发布求购
        发布求购
        点赞
        收藏
        wx-share
        分享

        Synthesis of Oligopeptides Containing an Oxirane Ring in the Place of a Peptidic Bond

        互联网

        1550
        Oligopeptides containing an oxirane ring have recently been identified as inhibitors of a variety of proteases ( 13 ). These peptidomimetics have the potential to coordinate with metal present in the active site and, after nucleophilic ring opening, irreversibly blocking the enzyme. For this reason, oxirane containing peptidomimetics are good candidates to became transition states analogs or suicide inhibitors with long term efficacy in vivo ( 3 ). Synthetic routes to a variety of terminal ( 48 ) and internal epoxide peptidomimetics ( 911 ) have been reported but there are no examples of incorporation of such epoxides into oligopeptides. The focus of this chapter will be on the preparation of oligopeptides (up to a three-peptide) containing an epoxide in the place of the peptide bond. The structures prepared here can be identified, using the notation suggested by Spatola ( 12 ) as AAxψ[ traws -epoxy]-AAy. The general synthetic approach described in this chapter is based on the aldol type reaction of a silylketene thioacetal and a β-amino α-selenyl aldehyde derived from an oligopeptide. This reaction stereoselectively generates a vicinal hydroxy selenide which can be further oxidized to epoxide (Fig. 1 ).
         
        Fig. 1.  Retrosynthetic analysis of oxirane peptidomimetrics.

        ad image
        提问
        扫一扫
        丁香实验小程序二维码
        实验小助手
        丁香实验公众号二维码
        扫码领资料
        反馈
        TOP
        打开小程序