Boc-Gly-Leu-NHMe | 146295-56-9

• 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: Boc-Gly-Leu-NHMe
• CAS: 146295-56-9
• 化学式: C₁₄H₂₇N₃O₄
• 分子量: 301.386
• InChiKey: OLQCSWBBRKCAIN-JTQLQIEISA-N

物化性质

• 沸点：
  531.9±35.0 °C(Predicted)
• 密度：
  1.058±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.79
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  96.53
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Boc-Gly-Leu-NHMe 在 20percent Pd(OH)2 on C 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 (2R,3R,4R,5R)-3,4-Dihydroxy-2,5-bis-{[((S)-3-methyl-1-methylcarbamoyl-butylcarbamoyl)-methyl]-carbamoyl}-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Studies on Novel Peptidomimetics Having Bi-directional Dispositions of Hydroxylated d-Pro-Gly Motifs Anchored on a C₂-Symmetric Iminosugar-Based Foundation

  摘要：

  A rigid pyrrolidine based scaffold comprising of 2,5-dideoxy-2,5-imino-D-idaric acid (1) is developed. Attachment of peptide strands to the carboxylic groups at both ends of this novel template led to the peptidomimetics 2 and 3. Conformational analysis by NMR studies revealed that compounds 2b, 3b and 2c, 3c take interesting turn structures (C-2 symmetric for 2c and 3c) in DMSO-d(6) consisting of identical intramolecular hydrogen bonds at two ends between LeuNH --> sugar-OH as depicted in structure A, whereas 2a and 3a display structures with regular beta-turns with hydrogen bonds between LeuNH --> Boc-C=O in one-half of their molecular frameworks (structure B), characteristic of the turn structures commonly observed in "D-Pro-Gly"-containing peptides. These results suggest that a cis hydroxyl group at the 3-position of the proline residue favors a pseudo,beta-turn-like nine-membered ring structure in hydroxyproline-containing peptides involving an intramolecular hydrogen bond between the hydroxyl and the i + 2 backbone amide.

  DOI：

  10.1021/jo010937y
• 作为产物：
  描述：

  BOC-甘氨酸 、 TFA^+-H-Leu-NHMe 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 120.0h， 以4.9 g的产率得到Boc-Gly-Leu-NHMe
  参考文献：
  名称：

  促进水中平行 β-片层二级结构的二酸接头

  摘要：

  我们报告了二酸单位的发展，这些单位促进了通过其 N 总站连接的肽段之间形成双链平行β-折叠二级结构。这些接头单元是通过将甘氨酸连接到顺式 1,2- 环己烷二甲酸 (CHDA) 的一个羧基而形成的。当 L-残基链以两种绝对构型中的任何一种连接到 CHDA-Gly 单元时，在水中观察到平行片形成。

  DOI：

  10.1021/ja802042c

文献信息

• Conformational Studies of Peptides Containing <i>cis</i>-3-Hydroxy-<scp>d</scp>-proline
  作者：T. K. Chakraborty、P. Srinivasu、R. Vengal Rao、S. Kiran Kumar、A. C. Kunwar

  DOI：10.1021/jo048893r

  日期：2004.10.1

  Conformational analysis of peptides containing cis-3-hydroxy-D-proline (D-cis-3-Hyp) by NMR studies revealed that the 3-hydroxyl group in this amino acid plays a significant role in the overall three-dimensional structures of the peptides. When the D-cis-3-Hyp had its 3-hydroxyl group protected as the benzyl (Bn) ether, the peptide displayed a beta-hairpin structure in both CDCl3 and DMSO-d(6). Even after the removal of the Bn group, the resulting deprotected compound retained the same structure as in the protected version in CDCl3. However, in polar solvent DMSO-d(6), the C-terminal strand of the hydroxyl-deprotected peptide flipped to the side of the hydroxyl group, breaking the hairpin to form a pseudo beta-turn-like nine-membered ring structure involving an intramolecular hydrogen bond between LeuNH --> HypC3-OH.