Ala-Thr(O-[Galβ1-3GalNAcα-1])-Ala | 259236-34-5

• 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: Ala-Thr(O-[Galβ1-3GalNAcα-1])-Ala
• 英文别名: L-alanyl-O-[β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-α-D-galactopyranosyl]-L-threonyl-L-alanine；L-alanyl-O-[β-D-galactopyranosyl-(1->3)-2-acetamide-2-deoxy-α-D-galactopyranosyl]-L-threonyl-L-alanine；(2S)-2-[[(2S,3R)-3-[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-[[(2S)-2-aminopropanoyl]amino]butanoyl]amino]propanoic acid
• CAS: 259236-34-5
• 化学式: C₂₄H₄₂N₄O₁₅
• 分子量: 626.615
• InChiKey: BDXZCHLLQCKPLR-DXGQJTDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7.3
• 重原子数：
  43
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  309
• 氢给体数：
  11
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  Ala-Thr(O-[Galβ1-3GalNAcα-1])-Ala 在 二苯基膦叠氮化物 作用下， 生成
  参考文献：
  名称：

  抗冻糖蛋白：阐明抗冻活性必不可少的结构基序。

  摘要：

  DOI：

  10.1002/anie.200353110
• 作为产物：
  描述：

  N-(benzyloxycarbonyl)-L-alanyl-O-[(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(1->3)-(2-acetamido-4,6-di-O-benzyl-2-deoxy-α-D-galactopyranosyl)]-L-threonyl-L-alanine benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以100%的产率得到Ala-Thr(O-[Galβ1-3GalNAcα-1])-Ala
  参考文献：
  名称：

  Efficient and versatile synthesis of mucin-like glycoprotein mimics

  摘要：

  An efficient synthetic method of sequential glycopeptide-polymer by means of the combined chemical and enzymatic strategy was applied to the practical synthesis of some tandem repeating mucin-type glycoproteins. Versatility of the present synthetic strategy was demonstrated by elucidating some physicochemical and conformational analyses of these synthetic mucins. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01359-5

文献信息

• One-pot synthesis of cyclic antifreeze glycopeptides
  作者：Masakazu Hachisu、Hiroshi Hinou、Manabu Takamichi、Sakae Tsuda、Shuhei Koshida、Shin-Ichiro Nishimura

  DOI：10.1039/b815917c

  日期：——

  The first cyclic glycopeptides exhibiting significant antifreeze activity by forming hexagonal-bipyramidal ice crystals, denoted cyclic antifreeze glycopeptides (cyclic AFGPs), were constructed by a one-pot synthesis based on the controlled cyclization reaction of pre-formed small linear glycopeptides.

  通过形成预形成的小线性糖肽的受控环化反应，通过一锅合成法构建了通过形成六方双锥体冰晶而显示出显着的抗冻活性的第一环状糖肽，即环状抗冻糖肽（环状AFGP）。
• Antifreeze Glycoproteins: Elucidation of the Structural Motifs That Are Essential for Antifreeze Activity
  作者：Yuki Tachibana、Garth L. Fletcher、Naoki Fujitani、Sakae Tsuda、Kenji Monde、Shin-Ichiro Nishimura

  DOI：10.1002/anie.200353110

  日期：2004.2.6
• Efficient and versatile synthesis of mucin-like glycoprotein mimics
  作者：Yuki Tachibana、Naoki Matsubara、Fumio Nakajima、Tetsuro Tsuda、Sakae Tsuda、Kenji Monde、Shin-Ichiro Nishimura

  DOI：10.1016/s0040-4020(02)01359-5

  日期：2002.12

  An efficient synthetic method of sequential glycopeptide-polymer by means of the combined chemical and enzymatic strategy was applied to the practical synthesis of some tandem repeating mucin-type glycoproteins. Versatility of the present synthetic strategy was demonstrated by elucidating some physicochemical and conformational analyses of these synthetic mucins. (C) 2002 Elsevier Science Ltd. All rights reserved.