Boc-Ser(Bzl)-Tyr(Bzl)-Glu-OH | 50715-57-6

• 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-Ser(Bzl)-Tyr(Bzl)-Glu-OH
• 英文别名: Boc-Ser(Bzl)-Tyr(Bzl)-Gly；2-[[(2S)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylmethoxypropanoyl]amino]-3-(4-phenylmethoxyphenyl)propanoyl]amino]acetic acid
• CAS: 50715-57-6
• 化学式: C₃₃H₃₉N₃O₈
• 分子量: 605.688
• InChiKey: AQKYLPBCIUTEPO-NSOVKSMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  44.0
• 可旋转键数：
  15.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  152.29
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Boc-Ser(Bzl)-Tyr(Bzl)-Glu-OH 在 1-羟基苯并三唑 、 苯甲醚 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.25h， 生成 pGlu-His-Trp-Ser-Tyr-Gly-Leu
  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 在 盐酸 、 氢氧化钾 、 TEA 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 33.16h， 生成 Boc-Ser(Bzl)-Tyr(Bzl)-Glu-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

文献信息

• Polymer-supported synthesis of protected peptide segments on a photosensitive o-nitro(a-methyl)bromobenzyl resin
  作者：A. Ajayaghosh、V.N. Rajasekharan Pillai

  DOI：10.1016/s0040-4020(01)90104-8

  日期：1988.1

  The preparation of a new polystyrene support containing the photodetachable -nitro(α -methyl)benzyl anchoring group and its application in the solid phase synthesis of fully protected C-terminal peptides are described, The preparation of the photosensitive resin involves a 4-step polymer-analogous reaction starting from 1 %-divinyl benzene crosslinked polystyrene. Amino acid units were incorporated

  描述了一种新型的含有光可分离的-硝基（α-甲基）苄基锚定基团的聚苯乙烯载体的制备及其在完全保护的C-末端肽的固相合成中的应用。光敏树脂的制备涉及4步聚合物-类似反应从1％-二乙烯基苯交联的聚苯乙烯开始。按照标准固相肽合成方法，将氨基酸单元掺入该树脂中，并在中性条件下于350 nm通过光解从载体上裂解肽，总收率为40％至50％。肽通过就位的仲酯键连接至硝基是允许肽从支持物光解裂解的因素。