Boc-Tyr(Bzl)-Gly-OBzl | 37579-77-4

• 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: Boc-Tyr(Bzl)-Gly-OBzl
• 英文别名: N-tert-Butyloxycarbonyl-O-benzyltyrosylglycine Benzyl Ester；benzyl 2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(4-phenylmethoxyphenyl)propanoyl]amino]acetate
• CAS: 37579-77-4
• 化学式: C₃₀H₃₄N₂O₆
• 分子量: 518.61
• InChiKey: CUZGZNWXTWKHAZ-SANMLTNESA-N

物化性质

• 沸点：
  707.3±60.0 °C(Predicted)
• 密度：
  1.183±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  38
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-Tyr(Bzl)-Gly-OBzl 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 0.08h， 以88%的产率得到N-Boc-Tyr(Bn)-Gly-OH
  参考文献：
  名称：

  An approach to the elucidation of metabolic breakdown products of the luteinizing hormone-releasing hormone

  摘要：

  Metabolic breakdown of the luteinizing hormone-releasing hormone (LH-RH) could lead to the following fragments containing pyroglutamic acid: pyroglutamic acid (1), pGlu-His (2), pGLu-His-Trp (3), pGlu-His-Trp-Ser (4), etc., and finally pGlu-His-Trp-Ser-Tyr-Gly-Leu-Arg-Pro-Gly (10). We have synthesized fragments 2-10 and successfully separated all ten metabolites and LH-RH by high-performance liquid chromatography (HPLC) with a muBondapak C18 column. In a test of the viability of the method, cochromatography of fragments 1-10 and LH-RH with the products of chymotryptic digestion of tritiated LH-RH showed radioactive peaks corresponding to the expected products, fragments 3 and 5. Analysis of the products of incubation of a rat kidney homogenate supernatant with LH-RH showed fragments 1-4 and LH-RH. The finding of breakdown at position 4 uncovers a new site of LH-RH breakdown and points the way to the design of potential LH-RH antagonists and agonists where the 4 position would be substituted with unnatural amino acids to prevent breakdown.

  DOI：

  10.1021/jm00138a009
• 作为产物：
  描述：

  Boc-O-苄基-L-酪氨酸 、 甘氨酸苄酯盐酸盐 在 TEA 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以82%的产率得到Boc-Tyr(Bzl)-Gly-OBzl
  参考文献：
  名称：

  An approach to the elucidation of metabolic breakdown products of the luteinizing hormone-releasing hormone

  摘要：

  Metabolic breakdown of the luteinizing hormone-releasing hormone (LH-RH) could lead to the following fragments containing pyroglutamic acid: pyroglutamic acid (1), pGlu-His (2), pGLu-His-Trp (3), pGlu-His-Trp-Ser (4), etc., and finally pGlu-His-Trp-Ser-Tyr-Gly-Leu-Arg-Pro-Gly (10). We have synthesized fragments 2-10 and successfully separated all ten metabolites and LH-RH by high-performance liquid chromatography (HPLC) with a muBondapak C18 column. In a test of the viability of the method, cochromatography of fragments 1-10 and LH-RH with the products of chymotryptic digestion of tritiated LH-RH showed radioactive peaks corresponding to the expected products, fragments 3 and 5. Analysis of the products of incubation of a rat kidney homogenate supernatant with LH-RH showed fragments 1-4 and LH-RH. The finding of breakdown at position 4 uncovers a new site of LH-RH breakdown and points the way to the design of potential LH-RH antagonists and agonists where the 4 position would be substituted with unnatural amino acids to prevent breakdown.

  DOI：

  10.1021/jm00138a009

文献信息

• Studies on amino acids and peptides-III. 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide, , as a new racemization free coupling reagent in peptide synthesis
  作者：U. Pedersen、M. Thorsen、E.-E.A.M. El-Khrisy、K. Clausen、S.-O. Lawesson

  DOI：10.1016/0040-4020(82)80104-x

  日期：1982.1

  of N-protected amino acids (Z-Gly-OH, Boc-Gly-OH, Boc-S-Ser(Bzl)-OH, Boc-S-Tyr(Bzl)-OH, Z-S-Arg(Z2)-OH, and Z-S-Pro-OH), at room temperature in CH2Cl2 to give the intermediates , mixed anhydrides. When is treated with two moles of a base and one mole of the salt of an amino acid ester (TosOH·H-Gly-OBzl, HCl·H-Gly-OBzl, HCl·H-Gly-OEt, and HCl·H-S-Phe-OtBu) at 0°C, the expected peptide is isolated in

  容易获得的2,4-双（4-甲氧基苯基）-1,3,2,4-二硫代二膦2,4-二硫已与N-保护的氨基酸的盐（Z-Gly-OH，Boc- Gly-OH，Boc-S-Ser（Bzl）-OH，Boc-S-Tyr（Bzl）-OH，ZS-Arg（Z 2）-OH和ZS-Pro-OH），在室温下于CH 2中Cl 2给出中间体，混合酸酐。当用碱的两摩尔和氨基酸酯的盐的一摩尔处理（TOSOH·H -甘氨酸- OBzl计，盐酸·H -甘氨酸- OBzl计，盐酸·H -甘氨酸- OET，和HCl·HS- Phe-OtBu）在0°C时，预期的肽被分离出来，产量高。还发现LR在Z-Gly-S-Ala-OH和TosOH·HS-Leu-OBzl之间的片段偶联中是有用的试剂。通过HPLC测试该三肽（不需要去保护和根据Izumiya的氨基酸分析），并且未观察到差向异构化（＜0.7％）。
• Synthetic decapeptide having the activity of the luteinizing hormone
  申请人：——

  公开号：US03953416A1

  公开（公告）日：1976-04-27

  A synthetic decapeptide, L-pglutamyl-L-histidyl-L-tryptophanyl-L-seryl-L-tyrosyl-glycyl-L-leucyl-L- arginyl-L-prolyl-glycinamide which has the hormonal activities of the luteinizing hormone releasing hormone (LRH) of the hypothalamus gland of mammals is produced by utilizing as the key starting materials, the amino acids, glutamic acid or pyroglutamic acid, histidine, tryptophan, serine, tyrosine, glycine, leucine, arginine, and proline. Synthesis of the decapeptide is accomplished by coupling, in appropriate combinations of appropriate protected forms of the amino acids, and finally deprotecting to yield the amide, L-pglutamyl-L-histidyl-L-tryptophanyl-L-seryl-L-tyrosyl-glycyl-L-leucyl-L- arginyl-L-prolyl-glycinamide.

  一种合成的十肽，L-谷氨酰-L-组氨酰-L-色氨酰-L-丝氨酰-L-酪氨酰-甘氨酰-L-亮氨酰-L-精氨酰-L-脯氨酰-甘胺酰，具有哺乳动物下丘脑腺体促黄体激素释放激素（LRH）的激素活性，其关键起始物质为氨基酸谷氨酸或吡二酰谷氨酸，组氨酸，色氨酸，丝氨酸，酪氨酸，甘氨酸，亮氨酸，精氨酸和脯氨酸。通过使用适当保护的氨基酸的适当组合进行耦合，最后去保护得到酰胺，从而完成十肽的合成，即L-谷氨酰-L-组氨酰-L-色氨酰-L-丝氨酰-L-酪氨酰-甘氨酰-L-亮氨酰-L-精氨酰-L-脯氨酰-甘胺酰。
• Pedersen, U.; Yde, B.; Andersen, T., Phosphorus and Sulfur and the Related Elements, 1983, vol. 18, p. 381 - 384
  作者：Pedersen, U.、Yde, B.、Andersen, T.、Thorsen, M.、Clausen, K.、Lawesson, S.-O.

  DOI：——

  日期：——
• US3953416A
  申请人：——

  公开号：US3953416A

  公开（公告）日：1976-04-27
• An approach to the elucidation of metabolic breakdown products of the luteinizing hormone-releasing hormone
  作者：Mary Alice Stetler-Stevenson、Dai Chang Yang、Andrew Lipkowski、Linda McCartney、Darryl Peterson、George Flouret

  DOI：10.1021/jm00138a009

  日期：1981.6

  Metabolic breakdown of the luteinizing hormone-releasing hormone (LH-RH) could lead to the following fragments containing pyroglutamic acid: pyroglutamic acid (1), pGlu-His (2), pGLu-His-Trp (3), pGlu-His-Trp-Ser (4), etc., and finally pGlu-His-Trp-Ser-Tyr-Gly-Leu-Arg-Pro-Gly (10). We have synthesized fragments 2-10 and successfully separated all ten metabolites and LH-RH by high-performance liquid chromatography (HPLC) with a muBondapak C18 column. In a test of the viability of the method, cochromatography of fragments 1-10 and LH-RH with the products of chymotryptic digestion of tritiated LH-RH showed radioactive peaks corresponding to the expected products, fragments 3 and 5. Analysis of the products of incubation of a rat kidney homogenate supernatant with LH-RH showed fragments 1-4 and LH-RH. The finding of breakdown at position 4 uncovers a new site of LH-RH breakdown and points the way to the design of potential LH-RH antagonists and agonists where the 4 position would be substituted with unnatural amino acids to prevent breakdown.