(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]-3-tritylsulfanylpropanoyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-3-tritylsulfanylpropanoyl]amino]-N-(2-amino-2-oxoethyl)-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutanamide | 1053256-63-5

• 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: (2S,3R)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]-3-tritylsulfanylpropanoyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-3-tritylsulfanylpropanoyl]amino]-N-(2-amino-2-oxoethyl)-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutanamide
• CAS: 1053256-63-5
• 化学式: C₇₆H₈₂N₈O₁₄S₂
• 分子量: 1395.66
• InChiKey: BZRYXQZUWWTUIX-OSVGAXPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  100
• 可旋转键数：
  33
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  414
• 氢给体数：
  13
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]-3-tritylsulfanylpropanoyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-3-tritylsulfanylpropanoyl]amino]-N-(2-amino-2-oxoethyl)-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutanamide 在 三氟乙酸 、 potassium hexacyanoferrate(III) 作用下， 以 ammonium hydroxide 、 乙腈 为溶剂， 生成 (4S,7S,13S)-13-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]-N-[(2S,3R)-1-[(2-amino-2-oxoethyl)amino]-1-oxo-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutan-2-yl]-7-benzyl-6,9,12-trioxo-1,2-dithia-5,8,11-triazacyclotetradecane-4-carboxamide
  参考文献：
  名称：

  Solid-Phase Synthesis of O-Linked Glycopeptide Analogues of Enkephalin

  摘要：

  The synthesis of 18 N-alpha -FMOC-amino acid glycosides for solid-phase glycopeptide assembly is reported. The glycosides were synthesized either from the corresponding O'Donnell Schiff bases or from N-alpha -FMOC-amino protected serine or threonine and the appropriate glycosyl bromide using Hanessian's modification of the Koenigs-Knorr reaction. Reaction rates of D-glycosyl bromides (e.g., acetobromoglucose) with the L- and D-forms of serine and threonine are distinctly different and can be rationalized in terms of the steric interactions within the two types of diastereomeric transition states for the D/L and D/D reactant pairs. The N-alpha -FMOC-protected glycosides [monosaccharides Xyl, Glc, Gal, Man, GlcNAc, and GalNAc; disaccharides Gal-beta (1-4)-Gle (lactose), Glc-beta-(1-4)-Glc (cellobiose), and Gal-alpha (1-6)-Glc (melibiose)] were incorporated into 22 enkephalin glycopeptide analogues. These peptide opiates bearing the pharmacophore H-Tyr-c[DCys-Gly-PheDCys]- were designed to probe the significance of the glycoside moiety and the carbohydrate-peptide linkage region in blood-brain barrier (BBB) transport, opiate receptor binding, and analgesia.

  DOI：

  10.1021/jo005712m