N-(正丁基)-L-蛋氨酸 | 103024-69-7

• 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
• 中文名称: N-(正丁基)-L-蛋氨酸
• 英文名称: N-(n-butyl)-L-methionine
• 英文别名: (2S)-2-(butylazaniumyl)-4-methylsulfanylbutanoate
• CAS: 103024-69-7
• 化学式: C₉H₁₉NO₂S
• 分子量: 205.321
• InChiKey: FVKIZZKHMXMSOE-QMMMGPOBSA-N

物化性质

• 沸点：
  342.9±37.0 °C(Predicted)
• 密度：
  1.053±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  L-蛋氨酸 在 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.17h， 生成 N-(正丁基)-L-蛋氨酸
  参考文献：
  名称：

  Sodium borohydride: A versatile reagent in the reductive N-monoalkylation of α-amino acids and α-amino methyl esters

  摘要：

  α-氨基酸和α-氨基甲酯可以通过还原缩合反应在存在苏打硼氢化钠的情况下，利用几种羰基化合物轻松转化为它们的N-单烷基衍生物。这种还原剂在轻微但必要的程序变化下显示出广泛的多功能性。该反应允许通过使用苏打硼氘化钠对新的N-取代基进行α-单氘标记。关键词：α-氨基酸，α-氨基甲酯，苏打硼氢化钠，还原性N-单烷基化，羰基化合物。

  DOI：

  10.1139/v02-083

文献信息

• Isozyme-specific enzyme inhibitors. 12. C- and N-methylmethionines as substrates and inhibitors of methionine adenosyltranferases of normal and hepatoma rat tissues
  作者：Hong Lim、Francis Kappler、Ton T. Hai、Alexander Hampton

  DOI：10.1021/jm00159a030

  日期：1986.9

  The 2-, 3-, and 4-mono-C-methyl derivatives of D,L-methionine (Met) have been resolved into the 10 possible enantiomeric forms having the configurations 2-Me-D, 2-Me-L, 3(alpha or beta)-Me-D, 3(alpha or beta)-Me-L, 4(alpha or beta)-Me-D, and 4(alpha or beta)-Me-L (the alpha designation was given to enantiomeric pairs that had higher Rf values on silica gel chromatograms than their diastereomeric counterparts). All compounds were weak, poorly selective inhibitors of the rat M-2 (normal tissue) and M-T (Novikoff ascitic hepatoma) variants of Met adenosyltransferase. Kinetic analysis of the three most effective showed them to be competitive inhibitors with respect to Met with both variants; the strongest inhibition (KM(Met)/Ki = 0.03) was that of M-T by 3 beta-Me-L-Met. The Me-Met enantiomers had low substrate efficiencies (Vmax/KM) in the range (0.5-2.2) X 10(-4) that of L-Met with M-2 (0.2-1.3) X 10(-3) with M-T among seven compounds studied. At a 4 mM level, seven of the enantiomers were converted to adenosylmethionine derivatives more rapidly by M-T than by M-2. Among these, 2-Me-L-Met, 3 alpha-Me-L-Met, 3 alpha-Me-D-Met, and 4 beta-Me-D-Met had little or no substrate activity with M-2. These differences in substrate specificity are potentially exploitable in the design of compounds with selective toxicity for rat tumor tissue. N-Me- and N-(n-Bu)-Met, and the Met analogue in which NH is substituted for S, were weak inhibitors of M-T and M-2 and showed no substrate activity at a level of 4 mM.
• Sodium borohydride: A versatile reagent in the reductive <i>N</i>-monoalkylation of α-amino acids and α-amino methyl esters
  作者：Giancarlo Verardo、Paola Geatti、Elena Pol、Angelo G Giumanini

  DOI：10.1139/v02-083

  日期：2002.7.1

  α-Amino acids and α-amino methyl esters are easily converted to their N-monoalkyl derivatives by a reductive condensation reaction using several carbonyl compounds in the presence of sodium borohydride. This reducing agent has shown a wide versatility with minor but essential procedural variations. The reaction allows the α-monodeuterium labeling of the new N-substituent by use of sodium borodeuteride.Key words: α-amino acid, α-amino methyl esters, sodium borohydride, reductive N-monoalkylation, carbonyl compounds.

  α-氨基酸和α-氨基甲酯可以通过还原缩合反应在存在苏打硼氢化钠的情况下，利用几种羰基化合物轻松转化为它们的N-单烷基衍生物。这种还原剂在轻微但必要的程序变化下显示出广泛的多功能性。该反应允许通过使用苏打硼氘化钠对新的N-取代基进行α-单氘标记。关键词：α-氨基酸，α-氨基甲酯，苏打硼氢化钠，还原性N-单烷基化，羰基化合物。