H-Gly-Val-Ala-OBn | 159922-58-4

• 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: H-Gly-Val-Ala-OBn
• 英文别名: benzyl (2S)-2-[[(2S)-2-[(2-aminoacetyl)amino]-3-methylbutanoyl]amino]propanoate
• CAS: 159922-58-4
• 化学式: C₁₇H₂₅N₃O₄
• 分子量: 335.403
• InChiKey: XQJRMCXXPWEAGI-WFASDCNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  111
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  H-Gly-Val-Ala-OBn 、 N-(9-fluorenylmethoxycarbonyl)-O-[(α,α-dimethyl-4-succin-monoamidobenzyl)dimethylsilyl]-L-serine allyl ester 生成 N-(9-fluorenylmethoxycarbonyl)-L-seryl-L-glycyl-L-valyl-L-alanine benzyl ester
  参考文献：
  名称：

  Design and synthesis of silyl ether-based linker for solid-phase synthesis of glycopeptides

  摘要：

  A novel silyl linker was designed to facilitate the solid-phase synthesis of protected glycopeptide blocks. Alcohols (carbohydrate, serine, or threonine) were silylated with trialkylchlorosilane containing the p-nitrophenyl group. The nitro group was reduced and succinylated to give the succinanilic acids, which were attached to the glycine-preloaded resin via activation with HBTU/HOBt. After elongation of the peptide chain by segment condensation or Fmoc chemistry-based stepwise method, the synthesized glycopeptides in the protected form were split from the resin by fluoridolysis. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02390-9
• 作为产物：
  描述：

  L-缬氨酸叔丁酯盐酸盐 在 吗啉 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 H-Gly-Val-Ala-OBn
  参考文献：
  名称：

  Synthesis of human M blood group antigenic glycopeptide

  摘要：

  A first total synthesis of N-terminal glycoheptapeptide of human glycophorin AM was accomplished by solution phase peptide condensation utilizing the tetrasaccharide-linked amino acid building blocks designed for Fmoc strategy.

  DOI：

  10.1016/s0040-4039(00)76897-3

文献信息

• A novel silyl linker: Motif for side chain tethered approach to solid-phase glycopeptide synthesis
  作者：Kazuhiko Nakamura、Akira Ishii、Yukishige Ito、Yoshiaki Nakahara

  DOI：10.1016/s0040-4020(99)00649-3

  日期：1999.9

  In order to facilitate the solid-phase syntheses of protected glycopeptide blocks, we designed a novel silyl linker, which allows the alcoholic side chain (carbohydrate, serine, or threonine) of (glyco-)peptides to link to the solid support. Utilizing this linker, peptide coupling reactions at both the N- and the C-termini were successful. Synthesis of the glycophorin AM fragment corresponding to the N-terminal glycoheptapeptide is demonstrated. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthesis of human M blood group antigenic glycopeptide
  作者：Yoshiaki Nakahara、Hiroyuki Iijima、Tomoya Ogawa

  DOI：10.1016/s0040-4039(00)76897-3

  日期：1994.5

  A first total synthesis of N-terminal glycoheptapeptide of human glycophorin AM was accomplished by solution phase peptide condensation utilizing the tetrasaccharide-linked amino acid building blocks designed for Fmoc strategy.
• Design and synthesis of silyl ether-based linker for solid-phase synthesis of glycopeptides
  作者：Kazuhiko Nakamura、Noriyasu Hanai、Masayuki Kanno、Aki Kobayashi、Yuki Ohnishi、Yukishige Ito、Yoshiaki Nakahara

  DOI：10.1016/s0040-4039(98)02390-9

  日期：1999.1

  A novel silyl linker was designed to facilitate the solid-phase synthesis of protected glycopeptide blocks. Alcohols (carbohydrate, serine, or threonine) were silylated with trialkylchlorosilane containing the p-nitrophenyl group. The nitro group was reduced and succinylated to give the succinanilic acids, which were attached to the glycine-preloaded resin via activation with HBTU/HOBt. After elongation of the peptide chain by segment condensation or Fmoc chemistry-based stepwise method, the synthesized glycopeptides in the protected form were split from the resin by fluoridolysis. (C) 1998 Elsevier Science Ltd. All rights reserved.