(2S)-N²-carbobenzoxy-N²-methyl-2,3-diaminopropionic acid | 147634-99-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S)-N²-carbobenzoxy-N²-methyl-2,3-diaminopropionic acid
• 英文别名: (S)-3-amino-2-(N-benzyloxycarbonyl-N-methyl)aminopropionic acid；(2S)-3-amino-2-[methyl(phenylmethoxycarbonyl)amino]propanoic acid
• CAS: 147634-99-9
• 化学式: C₁₂H₁₆N₂O₄
• 分子量: 252.27
• InChiKey: LIUNHXJYXPEHPN-JTQLQIEISA-N

物化性质

• 熔点：
  204 °C (decomp)(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  428.9±45.0 °C(Predicted)
• 密度：
  1.276±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  92.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S)-N²-carbobenzoxy-N²-methyl-2,3-diaminopropionic acid 在 sodium hydroxide 、 sodium carbonate 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 3.5h， 生成 benzyl N-[(2S)-1-[[(Z)-N-carbamoyl-C-methylsulfanylcarbonimidoyl]amino]-3-[(2-methylpropan-2-yl)oxycarbonylamino]-1-oxopropan-2-yl]-N-methylcarbamate
  参考文献：
  名称：

  First enantioselective synthesis of the novel antiinfective TAN-1057A via its aminomethyl-substituted dihydropyrimidinone heterocycle

  摘要：

  Enantiomerically pure N-2-Z-N-2-MeAsnOH [(S)-14], prepared in 8 steps (23% overall yield) from asparaginic acid, was first subjected to a Hofmann degradation with PhI(OCOCF3)(2) yielding (S)-N-2-Z-N-2-methyl-2,3-diaminopropanoic acid [N-2-Z-N-2-Me-L-A(2)pr, (S)-15], and this in turn was protected to give N-2-Z-N-3-Boc-N-2-Me-L-A(2)pr [(S)-17]. Condensation of (S)-17 with HN=C(SMe)NHCONH2 followed by removal of the tert-butoxycarbonyl protecting group, cyclization and hydrogenolytic removal of the Z-group gave the heterocycle of TAN-1057A [(S)-1] with an e.e. of 87 in 36% yield [from (S)-14]. Coupling of (S)-1 with (S)-tris-Z-beta-homoarginine (20a) in the presence of O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HATU) and iPr(2)NEt in N,N-dimethyl-acetamide followed by hydrogenolysis afforded the most active A-diastereomer of the natural antibiotic TAN-1057 in 52% yield (from (S)-1 and 20a). Similarly, starting from (S)-1, a single diastereomer of the potent, less toxic TAN-1057A analogue 22b with a beta-lysine side chain has been prepared. All described synthetic steps do not require column chromatography for purification of the products. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.034
• 作为产物：
  描述：

  2-L--3-phthalimidopropanoic acid 在 三正丁胺 、 sodium hydride 、 苯肼 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 54.0h， 生成 (2S)-N²-carbobenzoxy-N²-methyl-2,3-diaminopropionic acid
  参考文献：
  名称：

  A new anti-MRSA dipeptide, TAN-1057 A

  摘要：

  The chemical structure of a new dipeptide antibiotic, TAN-1057 A, isolated from the broth filtrate of Flexibacter sp. PK-74 was determined to be (3'S, 5S)-5-[N-methyl-N-(3'-amino-6'-guanidinohexanoyl)amino]-5,6-dihydro-2-ureido-4(1H)-pyrimidone. The antibiotic was specifically active against staphylococcus species including methicillin-resistant strains.

  DOI：

  10.1016/s0040-4020(01)80503-2

文献信息

• A new anti-MRSA dipeptide, TAN-1057 A
  作者：Yasunori Funabashi、Shigetoshi Tsubotani、Katsuo Koyama、Nozomi Katayama、Setsuo Harada

  DOI：10.1016/s0040-4020(01)80503-2

  日期：1993.1

  The chemical structure of a new dipeptide antibiotic, TAN-1057 A, isolated from the broth filtrate of Flexibacter sp. PK-74 was determined to be (3'S, 5S)-5-[N-methyl-N-(3'-amino-6'-guanidinohexanoyl)amino]-5,6-dihydro-2-ureido-4(1H)-pyrimidone. The antibiotic was specifically active against staphylococcus species including methicillin-resistant strains.
• First enantioselective synthesis of the novel antiinfective TAN-1057A via its aminomethyl-substituted dihydropyrimidinone heterocycle
  作者：Vladimir N. Belov、Michael Brands、Siegfried Raddatz、Jochen Krüger、Sofia Nikolskaya、Viktor Sokolov、Armin de Meijere

  DOI：10.1016/j.tet.2004.06.034

  日期：2004.8

  Enantiomerically pure N-2-Z-N-2-MeAsnOH [(S)-14], prepared in 8 steps (23% overall yield) from asparaginic acid, was first subjected to a Hofmann degradation with PhI(OCOCF3)(2) yielding (S)-N-2-Z-N-2-methyl-2,3-diaminopropanoic acid [N-2-Z-N-2-Me-L-A(2)pr, (S)-15], and this in turn was protected to give N-2-Z-N-3-Boc-N-2-Me-L-A(2)pr [(S)-17]. Condensation of (S)-17 with HN=C(SMe)NHCONH2 followed by removal of the tert-butoxycarbonyl protecting group, cyclization and hydrogenolytic removal of the Z-group gave the heterocycle of TAN-1057A [(S)-1] with an e.e. of 87 in 36% yield [from (S)-14]. Coupling of (S)-1 with (S)-tris-Z-beta-homoarginine (20a) in the presence of O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HATU) and iPr(2)NEt in N,N-dimethyl-acetamide followed by hydrogenolysis afforded the most active A-diastereomer of the natural antibiotic TAN-1057 in 52% yield (from (S)-1 and 20a). Similarly, starting from (S)-1, a single diastereomer of the potent, less toxic TAN-1057A analogue 22b with a beta-lysine side chain has been prepared. All described synthetic steps do not require column chromatography for purification of the products. (C) 2004 Elsevier Ltd. All rights reserved.