N-BOC-thioglycinyl-glycine benzyl ester | 83283-25-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-BOC-thioglycinyl-glycine benzyl ester
• 英文别名: BOC-Glyt-Gly-OBzl；Benzyl 2-[[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethanethioyl]amino]acetate
• CAS: 83283-25-4
• 化学式: C₁₆H₂₂N₂O₄S
• 分子量: 338.428
• InChiKey: HGPYCCRBGLONDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-BOC-thioglycinyl-glycine benzyl ester 在 盐酸 作用下， 以 乙醚 为溶剂， 生成 Benzyl 2-[(2-aminoethanethioyl)amino]acetate
  参考文献：
  名称：

  Thioamides:  Synthesis, Stability, and Immunological Activities of Thioanalogues of Imreg. Preparation of New Thioacylating Agents Using Fluorobenzimidazolone Derivatives

  摘要：

  Imreg (Tyr(1)-Gly(2)-Gly(3)) is a well-known immunostimulant, However, it possesses a short half-life. Stabilized analogues of Imreg were prepared by a regioselective insertion in which peptide bonds at position 1,2 or 2,3 were replaced by thioamide linkages. This was achieved by using new thioacylating agents based on thioacyl-fluoro-N-benzimidazolone. The synthesis and properties of these reagents are described herein. This peptide modification enhanced significantly the half-life of the thioanalogues relative to Imreg in blood. The thioanalogues and Imreg were tested in vitro in T and B cell proliferation assays and for their ability to stimulate cytotoxic T-lymphocytes (CTLs). Only thiotyrosyl glycyl glycine 11 displayed some activity as evidenced by a weak stimulation of CTLs. On the basis of this activity and the increased stability, an in vivo immunological evaluation was undertaken. Immunophenotyping of 11 revealed a significant increase in activated CTL and NK cell populations in the spleen. This expansion was also accompanied by a significant stimulation of NK cells and the B cell proliferative response. Thioanalogues of Imreg were generally nontoxic, as exemplified by 11. The latter is a promising immunostimulant which may be targeted for cancer and viral infections, where CTLs and NK cells play an important role, or as a vaccine adjuvant where stimulation of antibody-producing B cells is important.

  DOI：

  10.1021/jm9900467
• 作为产物：
  描述：

  N-(tert-butoxycarbonyl)glycylglycine benzyl ester 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以89%的产率得到N-BOC-thioglycinyl-glycine benzyl ester
  参考文献：
  名称：

  内硫肽

  摘要：

  的N-保护的二肽酯已被转换成相应的被保护endothiopeptides 1使用Lawesson试剂，2种的氨基和羧基去保护1.方法，以及与氨基酸的硫肽的联接已经被定义并用于制备新颖的两个例子的N-保护具有单个硫酰胺键的硫代三肽内酯。考虑了硫酰胺键对二肽酯构象的可能影响。

  DOI：

  10.1016/s0040-4020(01)91869-1

文献信息

• Thioamides:  Synthesis, Stability, and Immunological Activities of Thioanalogues of Imreg. Preparation of New Thioacylating Agents Using Fluorobenzimidazolone Derivatives
  作者：Boulos Zacharie、Mouna Lagraoui、Marika Dimarco、Christopher L. Penney、Lyne Gagnon

  DOI：10.1021/jm9900467

  日期：1999.6.1

  Imreg (Tyr(1)-Gly(2)-Gly(3)) is a well-known immunostimulant, However, it possesses a short half-life. Stabilized analogues of Imreg were prepared by a regioselective insertion in which peptide bonds at position 1,2 or 2,3 were replaced by thioamide linkages. This was achieved by using new thioacylating agents based on thioacyl-fluoro-N-benzimidazolone. The synthesis and properties of these reagents are described herein. This peptide modification enhanced significantly the half-life of the thioanalogues relative to Imreg in blood. The thioanalogues and Imreg were tested in vitro in T and B cell proliferation assays and for their ability to stimulate cytotoxic T-lymphocytes (CTLs). Only thiotyrosyl glycyl glycine 11 displayed some activity as evidenced by a weak stimulation of CTLs. On the basis of this activity and the increased stability, an in vivo immunological evaluation was undertaken. Immunophenotyping of 11 revealed a significant increase in activated CTL and NK cell populations in the spleen. This expansion was also accompanied by a significant stimulation of NK cells and the B cell proliferative response. Thioanalogues of Imreg were generally nontoxic, as exemplified by 11. The latter is a promising immunostimulant which may be targeted for cancer and viral infections, where CTLs and NK cells play an important role, or as a vaccine adjuvant where stimulation of antibody-producing B cells is important.
• Endothiopeptides
  作者：D.W. Brown、M.M. Campbell、C.V. Walker

  DOI：10.1016/s0040-4020(01)91869-1

  日期：1983.1

  N-protected dipeptide esters have been converted into the corresponding protected endothiopeptides1 using Lawesson's reagent,2 1. Methods of amino and carboxyl deprotection, and coupling of the thiopeptides with amino acids have been defined and used to prepare two examples of novel N-protected endothiotripeptide esters with a single thioamide link. Possible effects of the thioamide bond on the conformation

  的N-保护的二肽酯已被转换成相应的被保护endothiopeptides 1使用Lawesson试剂，2种的氨基和羧基去保护1.方法，以及与氨基酸的硫肽的联接已经被定义并用于制备新颖的两个例子的N-保护具有单个硫酰胺键的硫代三肽内酯。考虑了硫酰胺键对二肽酯构象的可能影响。