L-α-amino-β-hydroxypropanal | 21654-00-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: L-α-amino-β-hydroxypropanal
• 英文别名: L-Ser；SERE；(2S)-2-amino-3-hydroxypropanal
• CAS: 21654-00-2
• 化学式: C₃H₇NO₂
• 分子量: 89.0941
• InChiKey: UXPVGJOKPUABJV-GSVOUGTGSA-N

物化性质

• 沸点：
  265.0±30.0 °C(Predicted)
• 密度：
  1.158±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  丝氨醇 在 horse liver alcohol dehydrogenase 、 环己酮 、 NADH 、 1,4-二巯基-2,3-丁二醇 作用下， 生成 L-α-amino-β-hydroxypropanal
  参考文献：
  名称：

  Enantioselective oxidation of 1,2-diols to L-.alpha.-hydroxy acids using co-immobilized alcohol and aldehyde dehydrogenases as catalysts

  摘要：

  DOI：

  10.1021/jo00211a046

文献信息

• <i>N</i>-Chlorosuccinimide-Promoted Oxidative Decarboxylation of α-Amino Acids in Aqueous Alkaline Medium
  作者：M. S. Ramachandran、D. Easwaramoorthy、V. Rajasingh、T. S. Vivekanandam

  DOI：10.1246/bcsj.63.2397

  日期：1990.8

  Kinetics of oxidation of twelve α-amino acids (AA) by N-chlorosuccinimide (NClS) in aqueous alkaline media have been studied and compared with those of N-bromosuccinimide (NBS) oxidation. Analysis of the results shows that the observed rate of oxidation is first-order in [oxidant] and zero-order in [substrate]. The rate of oxidation increases with increase in [OH−]free in [NClS], the exception being the amino acids having β-alkyl substituent such as valine, leucine etc. Perusal of the results shows that NC1S/NBS reacts with α-amino acid anion to produce α-amino acyl hypohalite which then decomposes in the rate-determining step to give the products. The intermediate α-amino acyl hypohalite is identified by UV-visible absorption spectra. Glycine behaves differently from other amino acids in both oxidants. The proposed mechanism is consistent with the observed kinetics.

  十二种α-氨基酸（AA）在水性碱性介质中与N-氯琥珀酰亚胺（NClS）的氧化动力学进行了研究，并与N-溴琥珀酰亚胺（NBS）的氧化进行了比较。结果分析表明，观察到的氧化速率对[氧化剂]是一阶，对[底物]是零阶。在[NClS]中，氧化速率随着[OH−]自由浓度的增加而增加，例外的是具有β-烷基取代基的氨基酸，如缬氨酸、亮氨酸等。结果的仔细审阅显示，NClS/NBS与α-氨基酸阴离子反应生成α-氨基酰亚氯，这在速率决定步骤中分解生成产物。中间体α-氨基酰亚氯通过紫外可见吸收光谱被鉴定。甘氨酸在两种氧化剂中的行为与其他氨基酸有所不同。所提出的机理与观察到的动力学相一致。
• Proline-Containing Cyclopeptides from the Marine Sponge <i>Phakellia fusca</i>
  作者：Hong-Jun Zhang、Yang-Hua Yi、Gen-Jin Yang、Min-Ye Hu、Gui-Dong Cao、Fan Yang、Hou-Wen Lin

  DOI：10.1021/np9008267

  日期：2010.4.23

  Four new cyclopeptides, phakellistatins 15-18 (2-5), together with five known cyclopeptides, phakellistatin 13 (1), hymenistatin I, and hymenamides G, H, and J, were isolated from the South China Sea sponge Phakellia fusca. Their structures were elucidated by HR-ESIMS, NMR, and MALDI-TOF/TOF sequence analysis. The absolute configurations of the amino acid residues of 2-5 were assigned to be L by enantioselective HPLC analysis.