(S)-3-azido-2-methylpropanoic acid | 84506-44-5

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (S)-3-azido-2-methylpropanoic acid
• 英文别名: (2S)-3-azido-2-methylpropanoic acid
• CAS: 84506-44-5
• 化学式: C₄H₇N₃O₂
• 分子量: 129.118
• InChiKey: MSETUITVEZUPHK-VKHMYHEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  51.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-3-azido-2-methylpropanoic acid 、 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-β-D-galactopyranose hydrochloride 在 (1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylaminomorpholinocarbenium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以72%的产率得到1,3,4,6-tetra-O-acetyl-2-((S)-3-azido-2-methylpropanamido)-2-deoxy-β-D-galactopyranose
  参考文献：
  名称：

  Engineering Orthogonal Polypeptide GalNAc-Transferase and UDP-Sugar Pairs

  摘要：

  O-Linked alpha-N-acetylgalactosamine (O-GalNAc) glycans constitute a major part of the human glycome. They are difficult to study because of the complex interplay of 20 distinct glycosyltransferase isoenzymes that initiate this form of glycosylation, the polypeptide N-acetylgalactosaminyltransferases (GalNAc-Ts). Despite proven disease relevance, correlating the activity of individual GalNAc-Ts with biological function remains challenging due to a lack of tools to probe their substrate specificity in a complex biological environment. Here, we develop a "bump-hole" chemical reporter system for studying GalNAc-T activity in vitro. Individual GalNAc-Ts were rationally engineered to contain an enlarged active site (hole) and probed with a newly synthesized collection of 20 (bumped) uridine diphosphate N-acetylgalactosamine (UDP-GalNAc) analogs to identify enzyme-substrate pairs that retain peptide specificities but are otherwise completely orthogonal to native enzyme-substrate pairs. The approach was applicable to multiple GalNAc-T isoenzymes, including GalNAc-T1 and -T2 that prefer nonglycosylated peptide substrates and GalNAcT-10 that prefers a preglycosylated peptide substrate. A detailed investigation of enzyme kinetics and specificities revealed the robustness of the approach to faithfully report on GalNAc-T activity and paves the way for studying substrate specificities in living systems.

  DOI：

  10.1021/jacs.9b04695
• 作为产物：
  描述：

  (S)-3-叠氮基-2-甲基丙酸甲酯 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以63%的产率得到(S)-3-azido-2-methylpropanoic acid
  参考文献：
  名称：

  Solid-phase based synthesis of jasplakinolide analogs by intramolecular azide–alkyne cycloadditions

  摘要：

  本文描述了以1,2,3-三氮唑替代E型双键的jasplakinolide类似物聚焦库的合成，其中铜(I)催化叠氮-炔环加成反应作为一种高效的环化工具。

  DOI：

  10.1039/b710650e