(4S)-5-[[(2S,3R)-1-[[(2R,3S,5R,6R)-5-amino-6-[(1R,2S,3S,4R,6S)-4,6-diamino-3-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-3-hydroxyoxan-2-yl]methylamino]-3-hydroxy-1-oxobutan-2-yl]amino]-4-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]propanoyl]amino]-4-methylpentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoic acid | 950832-56-1

• 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: (4S)-5-[[(2S,3R)-1-[[(2R,3S,5R,6R)-5-amino-6-[(1R,2S,3S,4R,6S)-4,6-diamino-3-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-3-hydroxyoxan-2-yl]methylamino]-3-hydroxy-1-oxobutan-2-yl]amino]-4-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]propanoyl]amino]-4-methylpentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoic acid
• CAS: 950832-56-1
• 化学式: C₅₀H₈₃N₁₁O₁₉
• 分子量: 1142.27
• InChiKey: WYIKZGUVTBKDKD-OOIYVQJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.3
• 重原子数：
  80
• 可旋转键数：
  25
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  512
• 氢给体数：
  18
• 氢受体数：
  24

反应信息

• 作为产物：
  描述：

  尼拉霉素 、 YALPETGK 在 transpeptidase sortase A from Staphylococcus aureus Tris-HCl buffer 、 2-巯基乙醇 作用下， 反应 6.0h， 以73.5%的产率得到(4S)-5-[[(2S,3R)-1-[[(2R,3S,5R,6R)-5-amino-6-[(1R,2S,3S,4R,6S)-4,6-diamino-3-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-3-hydroxyoxan-2-yl]methylamino]-3-hydroxy-1-oxobutan-2-yl]amino]-4-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]propanoyl]amino]-4-methylpentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoic acid
  参考文献：
  名称：

  Peptide−Sugar Ligation Catalyzed by Transpeptidase Sortase:  A Facile Approach to Neoglycoconjugate Synthesis

  摘要：

  Glycoconjugate synthesis involving sugar and polypeptide remains a formidable challenge. Here we report a novel enzymatic method involving an unprecedented sortase-catalyzed transamidation reaction for site-specific engineering of sugars into native proteins. We show that sugars appended with a 6-aminohexose moiety can be efficiently ligated to peptides; and proteins encoded with a LPXTG sortase, recognition sequence. This robust reaction provides an elegant and simple approach for generating neoglycoproteins with an amide-linked sugar moiety at the carboxy terminus.

  DOI：

  10.1021/ja077358g