(2R,3S)-2-amino-3-methylpent-4-enoic acid | 221225-37-2

• 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: (2R,3S)-2-amino-3-methylpent-4-enoic acid
• 英文别名: (2R,3S)-2-Amino-3-methylpent-4-enoic acid
• CAS: 221225-37-2
• 化学式: C₆H₁₁NO₂
• 分子量: 129.159
• InChiKey: RXVINEUKGZXZAV-CRCLSJGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3S)-2-amino-3-methylpent-4-enoic acid 在 N,N'-羰基二咪唑 、 lithium diisopropyl amide 作用下， 生成 (4R,5S)-4-tert-Butoxycarbonylamino-5-methyl-3-oxo-hept-6-enoic acid benzyl ester
  参考文献：
  名称：

  A straightforward synthesis of protected isostatine from achiral precursors using the asymmetric chelate Claisen rearrangement

  摘要：

  Starting from achiral TFA-protected glycine crotyl ester (3) the interesting, suitable protected, enantiomerically pure beta-hydroxy-gamma-amino acid isostatine (7) was synthesized in only four steps. The amino acid obtained can directly be introduced into peptides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02486-1
• 作为产物：
  描述：

  (2R,3S)-(-)-3-Methyl-2-(trifluoroacetylamino)pent-4-enoic acid 在 sodium hydroxide 作用下， 生成 (2R,3S)-2-amino-3-methylpent-4-enoic acid
  参考文献：
  名称：

  A straightforward synthesis of protected isostatine from achiral precursors using the asymmetric chelate Claisen rearrangement

  摘要：

  Starting from achiral TFA-protected glycine crotyl ester (3) the interesting, suitable protected, enantiomerically pure beta-hydroxy-gamma-amino acid isostatine (7) was synthesized in only four steps. The amino acid obtained can directly be introduced into peptides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02486-1

文献信息

• Asymmetric β‐Methylation of <scp>l</scp> ‐ and <scp>d</scp> ‐α‐Amino Acids by a Self‐Contained Enzyme Cascade
  作者：Cangsong Liao、Florian P. Seebeck

  DOI：10.1002/anie.201916025

  日期：2020.4.27

  AbstractThis report describes a modular enzyme‐catalyzed cascade reaction that transforms l‐ or d‐α‐amino acids to β‐methyl‐α‐amino acids. In this process an α‐amino acid transaminase, an α‐keto acid methyltransferase, and a halide methyltransferase cooperate in two orthogonal reaction cycles that mediate product formation and regeneration of the cofactor pyridoxal‐5′‐phosphate and the co‐substrate S‐adenosylmethionine. The only stoichiometric reagents consumed in this process are the unprotected l‐ or d‐α‐amino acid and methyl iodide.
• Diastereoselective amidoallylation of glyoxylic acid with chiral tert-butanesulfinamide and allylboronic acid pinacol esters: efficient synthesis of optically active γ,δ-unsaturated α-amino acids
  作者：Shigeo Sugiyama、Saori Imai、Keitaro Ishii

  DOI：10.1016/j.tetasy.2013.07.026

  日期：2013.9

  A convenient synthesis of delta,gamma-unsaturated amino acids has been developed. After a mixture of (R)-tert-butanesulfinamide and glyoxylic acid with molecular sieves in CH2Cl2 was stirred for 42 h at room temperature, allylboronic acid pinacol ester was added to the mixture to give (R)-2-((R)-tert-butanesulfinamido)pent-4-enoic acid with high diastereoselectivity. The corresponding reaction of (Z)-crotylboronic acid pinacol ester produced no product; however, that of (E)-crotylboronic acid pinacol ester produced (2R,3S)-2-((R)-tert-butylsulfinamido)-3-methylpent-4-enoic acid with excellent diastereoselectivity. (C) 2013 Elsevier Ltd. All rights reserved.
• A straightforward synthesis of protected isostatine from achiral precursors using the asymmetric chelate Claisen rearrangement
  作者：Uli Kazmaier、Achim Krebs

  DOI：10.1016/s0040-4039(98)02486-1

  日期：1999.1

  Starting from achiral TFA-protected glycine crotyl ester (3) the interesting, suitable protected, enantiomerically pure beta-hydroxy-gamma-amino acid isostatine (7) was synthesized in only four steps. The amino acid obtained can directly be introduced into peptides. (C) 1998 Elsevier Science Ltd. All rights reserved.