3-(2-tert-Butoxycarbonylamino-2-methyl-propionylamino)-propionic acid | 532435-26-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: 3-(2-tert-Butoxycarbonylamino-2-methyl-propionylamino)-propionic acid
• 英文别名: 3-[[2-(Tert-butoxycarbonylamino)-2-methyl-propanoyl]amino]propanoic acid；3-[[2-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]propanoic acid
• CAS: 532435-26-0
• 化学式: C₁₂H₂₂N₂O₅
• 分子量: 274.317
• InChiKey: KDVDUAFCAVHBSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N'-二环己基碳二亚胺 、 3-(2-tert-Butoxycarbonylamino-2-methyl-propionylamino)-propionic acid 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以60%的产率得到tert-butyl N-{2-[N-(N,N'-dicyclohexyl-ureidocarbonylethyl)carbamoyl]prop-2-yl}carbamate
  参考文献：
  名称：

  Conformational heterogeneity of a turn mimetic pseudo-peptide: comparison of crystal state, solution and theoretically derived structures

  摘要：

  Crystal structure analysis of the pseudo-peptide (tert-Buty N-{2-[N-N,N'-dicyclohexyl-ureidocarbonylethyl)carbamoyl]-prop-2-yl}carbamate) exhibited presence of a 13-membered intramolecular hydrogen bonded structure involving Boc C=O and Urea NH group to form an alpha-turn mimic [Acta. Crystallogr. C 56 (2000) 1120]. However, NMR studies of this compound in CDCl3 using DMSO solvent titration of amide NH groups have revealed that the pseudo-peptide lacks of unique conformational. state in solution. We have therefore carried out ab initio quantum mechanical calculations at up to B3LYP/6-31G** using density function theory level to characterise relative stabilities of different possible conformations with distinctive hydrogen bonding patterns. Computational studies also reveal that a 13-atom hydrogen bonded turn, identical to the crystal state conformation and analogous to the alpha-turn (in proteins) is energetically most stable. The structures with 7-atom hydrogen bonded turn (gamma-turn) and with bifurcated hydrogen bonds are, however, seen to have energies quite comparable to that of the alpha-turn mimetic. This indicates possibility of existence of multiple conformational states, corresponding to various turn structures (viz. alpha-turn mimetic, gamma-turn, etc.) which may interconvert in NMR time scale. (C) 2003 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-2860(02)00619-1
• 作为产物：
  描述：

  t-Boc-Aib-β-Ala-OMe 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以75%的产率得到3-(2-tert-Butoxycarbonylamino-2-methyl-propionylamino)-propionic acid
  参考文献：
  名称：

  Conformational heterogeneity of a turn mimetic pseudo-peptide: comparison of crystal state, solution and theoretically derived structures

  摘要：

  Crystal structure analysis of the pseudo-peptide (tert-Buty N-{2-[N-N,N'-dicyclohexyl-ureidocarbonylethyl)carbamoyl]-prop-2-yl}carbamate) exhibited presence of a 13-membered intramolecular hydrogen bonded structure involving Boc C=O and Urea NH group to form an alpha-turn mimic [Acta. Crystallogr. C 56 (2000) 1120]. However, NMR studies of this compound in CDCl3 using DMSO solvent titration of amide NH groups have revealed that the pseudo-peptide lacks of unique conformational. state in solution. We have therefore carried out ab initio quantum mechanical calculations at up to B3LYP/6-31G** using density function theory level to characterise relative stabilities of different possible conformations with distinctive hydrogen bonding patterns. Computational studies also reveal that a 13-atom hydrogen bonded turn, identical to the crystal state conformation and analogous to the alpha-turn (in proteins) is energetically most stable. The structures with 7-atom hydrogen bonded turn (gamma-turn) and with bifurcated hydrogen bonds are, however, seen to have energies quite comparable to that of the alpha-turn mimetic. This indicates possibility of existence of multiple conformational states, corresponding to various turn structures (viz. alpha-turn mimetic, gamma-turn, etc.) which may interconvert in NMR time scale. (C) 2003 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-2860(02)00619-1

文献信息

• <i>tert</i>-Butyl<i>N</i>-{2-[<i>N</i>-(<i>N</i>,<i>N</i>′-dicyclohexylureidocarbonylethyl)carbamoyl]prop-2-yl}carbamate
  作者：Rahul Banerjee、Samir Kumar Maji、Arindam Banerjee

  DOI：10.1107/s0108270100007447

  日期：2000.9.15

  The title compound, C25H44N4O5, exhibits a turn with the main chain reversing direction, held together by an intramolecular N-H ... O hydrogen bond. In the urea fragment, a notable amide C-N bond between the carboxyl C and the tertiary N atom shows marked single-bond character [1.437 (2) Angstrom]. The dihedral angle of the beta-alanyl residue, centrally located in the turn, is gauche [69.2 (2)degrees]. The packing is mediated by two intermolecular hydrogen bonds and van der Waals contacts involving the methyl moieties and the cyclohexyl rings.
• Conformational heterogeneity of a turn mimetic pseudo-peptide: comparison of crystal state, solution and theoretically derived structures
  作者：Samir Kumar Maji、Debasish Haldar、Dhananjay Bhattacharyya、Arindam Banerjee

  DOI：10.1016/s0022-2860(02)00619-1

  日期：2003.2

  Crystal structure analysis of the pseudo-peptide (tert-Buty N-2-[N-N,N'-dicyclohexyl-ureidocarbonylethyl)carbamoyl]-prop-2-yl}carbamate) exhibited presence of a 13-membered intramolecular hydrogen bonded structure involving Boc C=O and Urea NH group to form an alpha-turn mimic [Acta. Crystallogr. C 56 (2000) 1120]. However, NMR studies of this compound in CDCl3 using DMSO solvent titration of amide NH groups have revealed that the pseudo-peptide lacks of unique conformational. state in solution. We have therefore carried out ab initio quantum mechanical calculations at up to B3LYP/6-31G** using density function theory level to characterise relative stabilities of different possible conformations with distinctive hydrogen bonding patterns. Computational studies also reveal that a 13-atom hydrogen bonded turn, identical to the crystal state conformation and analogous to the alpha-turn (in proteins) is energetically most stable. The structures with 7-atom hydrogen bonded turn (gamma-turn) and with bifurcated hydrogen bonds are, however, seen to have energies quite comparable to that of the alpha-turn mimetic. This indicates possibility of existence of multiple conformational states, corresponding to various turn structures (viz. alpha-turn mimetic, gamma-turn, etc.) which may interconvert in NMR time scale. (C) 2003 Elsevier Science B.V. All rights reserved.