Boc-Tyr-Gly-Gly-OBzl | 60566-43-0

• 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: Boc-Tyr-Gly-Gly-OBzl
• 英文别名: Tert-butyloxycarbonyltyrosyl-glycyl-glycine Benzyl Ester；N-BOC-L-tyrosinyl-glycinyl-glycine benzyl ester；N-t-butoxycarbonyl-L-tyrosylglycylglycine benzyl ester；benzyl 2-[[2-[[(2S)-3-(4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]acetyl]amino]acetate
• CAS: 60566-43-0
• 化学式: C₂₅H₃₁N₃O₇
• 分子量: 485.537
• InChiKey: NTVNZRPHJDNNAH-FQEVSTJZSA-N

物化性质

• 熔点：
  104-106 °C(Solv: ethyl acetate (141-78-6); ethyl ether (60-29-7))
• 沸点：
  764.5±60.0 °C(Predicted)
• 密度：
  1.241±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  143
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Boc-Tyr-Gly-Gly-OBzl 在 二丙硫醚 、 茴香硫醚 、 氢氟酸 、 苯甲醚 作用下， 反应 1.0h， 生成 L-酪氨酰甘氨酰甘氨酸
  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 盐酸 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 三乙胺 作用下， 以 乙醚 为溶剂， 生成 Boc-Tyr-Gly-Gly-OBzl
  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

文献信息

• Preparation and properties of three analogues of [5-leucine]enkephalin, substrates for enzyme conversion studies
  作者：Jaroslav Vičar、Linda Servítová、Martin Flegel、Karel Hauzer、Tomislav Barth

  DOI：10.1135/cccc19851329

  日期：——

  Analogues of [5-Leu]enkephalin, prolonged by methionine on the N-terminus or, by lysine or methionine on the C-terminus were prepared by fragment condensation, purified by ion exchange chromatography or high-pressure liquid chromatography. The substances were characterised by their opioid activity in a test on guinea-pig ileum in comparison with the activity of [5-Leu]enkephalin.

  将[5-Leu]enkephalin的类似物，通过在N-末端延长甲硫氨酸，或者通过在C-末端延长赖氨酸或甲硫氨酸，通过片段缩合制备，通过离子交换色谱或高压液相色谱纯化。这些物质通过与[5-Leu]enkephalin的活性在豚鼠回肠上的测试进行比较，以确定它们的阿片活性。
• 4-Substituted enkephalin derivatives
  申请人：G. D. Searle & Co.

  公开号：US04092304A1

  公开（公告）日：1978-05-30

  Analogs of methionine.sup.5 -enkephalin and leucine.sup.5 -enkephalin wherein the L-phenylalanyl residue in position 4 has been substituted by various other amino acid residues are disclosed herein. These analogs exhibit agonist activity at opiate receptor sites and are thus useful as analgesics, non-addicting narcotic antagonists and anti-diarrheal agents.

  本文披露了甲硫氨酸.sup.5-内啡肽和亮氨酸.sup.5-内啡肽的类似物，其中在第4位的L-苯丙氨酰残基被各种其他氨基酸残基替代。这些类似物在阿片受体位点表现出激动剂活性，因此可用作镇痛剂、非成瘾性镇痛拮抗剂和抗腹泻药物。
• Membrane-assisted receptor subtype selection: synthesis, membrane structure, and opioid receptor affinity of [Phe8,12]- and [Phe8,12, Lys10]dynorphin-(1–13)-tridecapeptide
  作者：Kiichiro Nakajima、Daniel Erne、John W. Bean、David F. Sargent、Robert Schwyzer、Stewart J. Paterson、Hans W. Kosterlitz

  DOI：10.1016/s0040-4020(01)86112-3

  日期：1988.1
• NAKAJIMA, KIICHIRO;ERNE, DANIEL;BEAN, JOHN W.;SARGENT, DAVID F.;SCHWYZER,+, TETRAHEDRON, 44,(1988) N 3, 721-732
  作者：NAKAJIMA, KIICHIRO、ERNE, DANIEL、BEAN, JOHN W.、SARGENT, DAVID F.、SCHWYZER,+

  DOI：——

  日期：——
• US4092304A
  申请人：——

  公开号：US4092304A

  公开（公告）日：1978-05-30