(3-hydroxy-5-hydroxymethyl-2-methylpyridin-4-ylmethyl)carbamic acid tert-butyl ester | 210034-86-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (3-hydroxy-5-hydroxymethyl-2-methylpyridin-4-ylmethyl)carbamic acid tert-butyl ester
• 英文别名: tert-Butyl ((3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl)methyl)carbamate；tert-butyl N-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]carbamate
• CAS: 210034-86-9
• 化学式: C₁₃H₂₀N₂O₄
• 分子量: 268.313
• InChiKey: ZTHWMXLIBPGNRK-UHFFFAOYSA-N

物化性质

• 溶解度：
  可溶于氘代氯仿，DCM

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  91.7
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3-hydroxy-5-hydroxymethyl-2-methylpyridin-4-ylmethyl)carbamic acid tert-butyl ester 在 咪唑 、 lithium hydroxide 、 四丁基氟化铵 、 sodium hydride 、 三乙胺 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-2-{(R)-2-((S)-2-Acetylamino-3-phenyl-propionylamino)-3-[4-(tert-butoxycarbonylamino-methyl)-5-methoxymethoxy-6-methyl-pyridin-3-ylmethylsulfanyl]-propionylamino}-propionic acid methyl ester
  参考文献：
  名称：

  Chiral polyamines from reduction of polypeptides: asymmetric pyridoxamine-mediated transaminations

  摘要：

  (BH3THF)-T-可以将多肽还原为多胺，同时保留手性。所得的多胺类物质是非常有趣的手性催化通用平台，鉴于其多样化的结构和相对容易合成的特性。我们已经构建了基于还原肽的多种手性吡哆胺催化剂。这些化合物能够以中等到良好的对映选择性进行α-酮酸的氨基转换，而其肽类同类物则几乎不具有手性诱导能力。© 2005 Elsevier Ltd. 保留所有权利。

  DOI：

  10.1016/j.bmcl.2005.01.021
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 pyridoxamine dihydrochloride 在 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 以95%的产率得到(3-hydroxy-5-hydroxymethyl-2-methylpyridin-4-ylmethyl)carbamic acid tert-butyl ester
  参考文献：
  名称：

  Dendrimeric Pyridoxamine Enzyme Mimics

  摘要：

  PAMAM dendrimers from generations 1-6 were synthesized with pyridoxamine in their core. They transaminated pyruvic and phenylpyruvic acids in water to alanine and phenylalanine, respectively, with Michaelis-Menten kinetics and high effectiveness compared with simple pyridoxamine. The largest dendrimers-similar in size to some globular proteins-were comparable in effectiveness to a previous polyethylenimine (PEI)-pyridoxamine catalyst, and to a protein-pyridoxamine catalyst, but not as effective as a previous PEI-pyridoxamine carrying lauryl hydrophobic groups. The new catalysts showed both general acid/base catalysis by their amino groups and hydrophobic binding of the phenylpyruvate substrate.

  DOI：

  10.1021/ja0374473

文献信息

• Reversal of optical induction in transamination by regioisomeric bifunctionalized cyclodextrins
  作者：Elisabetta Fasella、Steven D. Dong、Ronald Breslow

  DOI：10.1016/s0968-0896(98)00193-x

  日期：1999.5

  addition from their side, rather than acting to protonate the transamination intermediates. Related cyclodextrin-pyridoxamine compounds had been reported carrying ethylenediamine units instead of imidazoles, and high enantioselectivities in transamination were claimed. Our work indicates that these claims are incorrect, and that only poor selectivities are seen that are often unrelated to the position of the

  已经合成了两种异构化合物，它们在β-环糊精的C-6上带有吡ido胺，在相邻葡萄糖残基的C-6上带有咪唑单元。每个立体选择性地氨基苯丙酮酸转氨生成苯丙氨酸，并且具有相反的立体化学偏好。通过X射线晶体学和NMR光谱的结构确定表明，咪唑单元起从其侧面阻止质子加成的作用，而不是起质子化转氨中间体的作用。据报道，相关的环糊精-吡啶氧胺化合物带有乙二胺单元而不是咪唑，并要求在转氨反应中具有高对映选择性。我们的工作表明这些说法是不正确的，只能看到选择性差，通常与乙二胺单元的位置无关。
• Transamination Reactions with Multiple Turnovers Catalyzed by Hydrophobic Pyridoxamine Cofactors in the Presence of Polyethylenimine Polymers
  作者：Lei Liu、Wenjun Zhou、Jason Chruma、Ronald Breslow

  DOI：10.1021/ja048671a

  日期：2004.7.1

  Pyridoxamines carrying hydrophobic side chains reversibly bind into the hydrophobic core of polyethylenimines and transaminate ketoacids to amino acids with as much as a 725000-fold rate acceleration. Turnover catalysis was achieved by sacrificial oxidative decarboxylation of C-substituted amino acids, which reconverted the pyridoxals to pyridoxamines.
• Hydrophobic and electronic factors in the design of dialkylglycine decarboxylase mimics
  作者：Jason J. Chruma、Lei Liu、Wenjun Zhou、Ronald Breslow

  DOI：10.1016/j.bmc.2005.05.019

  日期：2005.10

  The first functional catalytic mimic of the enzyme dialkylglycine decarboxylase is described. This system utilizes a hydrophobically modified polyethylenimine polymer, a pyridoxamine cofactor, and a 2-aryl-2-alkylglycine sacrificial amine source to convert alpha-keto acids to alpha-amino acids at biologically relevant temperatures with multiple turnovers of the pyridoxamine catalyst. The effects of hydrophobic and electronic factors in the 2,2-disubstituted sacrificial amine source and the pyridoxamine catalyst on turnover frequency and turnover number are explored. (c) 2005 Elsevier Ltd. All rights reserved.