tert-butlyoxycarbonyl-Gly-Aib-OH | 74814-21-4

• 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: tert-butlyoxycarbonyl-Gly-Aib-OH
• 英文别名: Boc-Gly-Aib-OH；Boc-Gly-Aib；2-Methyl-2-[[2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]amino]propanoic acid
• CAS: 74814-21-4
• 化学式: C₁₁H₂₀N₂O₅
• 分子量: 260.29
• InChiKey: KSYURJHPBVVSKM-UHFFFAOYSA-N

物化性质

• 沸点：
  483.5±30.0 °C(Predicted)
• 密度：
  1.166±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  tert-butlyoxycarbonyl-Gly-Aib-OH 在 palladium on activated charcoal 盐酸 、 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 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 A-CH2CO-(Gly-Aib)6-NHCH2-D
  参考文献：
  名称：

  Tamiaki, Hitoshi; Maruyama, Kazuhiro, Journal of the Chemical Society. Perkin transactions I, 1991, # 4, p. 817 - 822

  摘要：

  DOI：
• 作为产物：
  描述：

  Boc-Gly-Aib-OBzl 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以60%的产率得到tert-butlyoxycarbonyl-Gly-Aib-OH
  参考文献：
  名称：

  Novel analogs of enkephalin: identification of functional groups required for biological activity

  摘要：

  Novel tri- and tetrapeptide analogues of enkephalin, in conjunction with earlier structure-activity data, confirm that chemical substitutents present in the first and fourth residues of enkephalin are required for in vitro biological activity. A class of arylamino and alkylamino derivatized tripeptides also were found to have significant in vitro opioid-like activity indistinguishable from [D-Ala2,D-Leu5]enkephalin and morphine.

  DOI：

  10.1021/jm00184a010

文献信息

• Intramolecular Photocyclization in Quinone-Bearing Oligopeptides
  作者：Hitoshi Tamiaki、Masakazu Hashimoto、Kazuhiro Maruyama

  DOI：10.1246/bcsj.67.1987

  日期：1994.7

  The photoexcited anthraquinone moiety (AQ) of (N-acetylglycyl)oligopeptide-linked anthraquinones in acetonitrile abstracted intramolecularly the hydrogen in the α-methylene of glycine to give a sole isomeric ring-closure product. Site-selectivity was produced mainly by a difference in the spatial distance between the C=O of AQ and reactive CH2.

  在乙腈中，(N-乙酰基甘氨酰)寡肽连接的蒽醌的蒽醌部分(AQ)被光激发后，从甘氨酸的α-亚甲基内部抽取氢，生成唯一的异构环化产物。这种位点选择性主要是由于AQ的C=O与反应性CH2之间的空间距离差异所导致的。
• Peptidomimetic design of unusual turns by incorporating flexible and rigid ω-amino acids simultaneously
  作者：Sudeshna Kar、Michael G.B. Drew、Animesh Pramanik

  DOI：10.1016/j.molstruc.2009.10.029

  日期：2010.1

  Boc-γAbu-Aib- m -ABA-OMe ( III ) (Aib: α-aminoisobutyric acid, βAla: β-alanine, γAbu: γ-aminobutyric acid, m -ABA: meta -aminobenzoic acid) with homologated amino acids at the N-terminus, the rigid γ-amino acid m -ABA at the C-terminus and the helicogenic Aib at the central position have been chosen to create unusual turns. Single crystal X-ray diffraction studies, solvent dependent NMR titrations and

  摘要 Boc-Gly-Aib-m-ABA-OMe(I)、Boc-βAla-Aib-m-ABA-OMe(II)和Boc-γAbu-Aib-m-ABA-OMe(III)(Aib: α-氨基异丁酸，βAla：β-丙氨酸，γAbu：γ-氨基丁酸，m-ABA：间氨基苯甲酸）在 N 端具有同源氨基酸，刚性 γ-氨基酸 m-ABA 在 C-终点和中心位置的螺旋 Aib 已被选择来创造不寻常的转弯。单晶 X 射线衍射研究、溶剂依赖的 NMR 滴定和 2D NMR 分析表明，肽 II 和 III 采用由修饰的 4 → 1 型分子内氢键稳定的不寻常的 11 和 12 元环。液相研究表明肽 I 存在于由 10 元分子内氢键稳定的 β-转角构象中。
• Intramolecular photoreaction of synthetic oligopeptide-linked anthraquinone molecules
  作者：Kazuhiro Maruyama、Masakazu Hashimoto、Hitoshi Tamiaki

  DOI：10.1021/jo00049a019

  日期：1992.11

  Photoreaction of (N-acetylglycyl)oligopeptide-linked anthraquinone molecules was investigated. In an acetonitrile site of glycine residue. The biradical formed was followed by the formation of C-O bonding via radical recombination to produce ring-closure products in high yields (23-58%). A variety of oligopeptide spacers between acetylglycine and anthraquinone moieties were systematically changed, and their photoreactivities were investigated. The isolated ring-closure products showed a site-selectivity in the photoreaction; one of the carbonyl groups of anthraquinone moiety coupled with the methylene group predominantly (the selectivity was 88/12-100/0). The efficiency of the photocyclization was dependent upon the size and the sequence of the oligopeptide spacer. These results showed that the oligopeptide spacer might control the distance and the orientation among the reaction sites, glycine methylene, and anthraquinone carbonyl groups.
• Two alternative conformational states of α,α-dialkylglycyl-<scp>L</scp>-prolyl sequences governed by presence/absence of an NH group directly following the proline residue. X-Ray crystal and molecular structures of Boc-<scp>D</scp>-Iva-<scp>L</scp>-Pro-NHBzl and Boc-<scp>L</scp>-Iva-<scp>L</scp>-Pro-NHBzl
  作者：Masao Kawai、Yoshimasa Omori、Hatsuo Yamamura、Yasuo Butsugan、Tooru Taga、Yoshihisa Miwa

  DOI：10.1039/p19950002115

  日期：——

  The crystal structures of the isovaline-containing dipeptides, Boc-D-Iva-L-Pro-NHBzl 4 and Boc-L-Iva-L-Pro-NHBzl 5 were determined by X-ray diffraction. The diastereoisomeric peptides adopt intramolecular hydrogen-bonded beta-turn conformations closely similar to each other (4:phi(Iva) -51 degrees, psi(Iva) -38 degrees, phi(Pro) - 70 degrees and psi(Pro) -17 degrees and 5:phi(Iva) -53 degrees, psi(Iva) -35 degrees, phi(Pro) -72 degrees and psi(Pro) -14 degrees). The Pro ring of each peptide is in CY-exo conformation. These conformations are essentially the same as those in the reported crystal structures of the Aib-L-Pro sequence possessing an NH group directly attached to the carbonyl of the L-Pro, indicating that replacement of either one of the two methyl groups of the Aib moiety with an ethyl group does not cause any significant change in the beta-turn conformation of the Aib-L-Pro sequence in the crystalline state.CD spectral analysis of the terminal chromophoric group-carrying peptides Dnp-Gly-X-L-Pro-Gly-pNA (X = Aib 6 and D/L-Iva 7/8) has shown that these three tetrapeptides in CHCl3 and THF solutions also adopt a beta-turn-type conformation. CD spectra of glycolic acid residue-containing analogues in place of the fourth Gly residue revealed a lack of beta-turn tendency in these analogues, indicating the importance of intramolecular hydrogen bonding for the beta-turn conformation of the central dipeptide moieties. The results are consistent with the reported unturned crystal structures of Aib-L-Pro and D/L-Iva-L-Pro sequence-containing peptides tacking the NH group which directly follows the Pro residue available for intramolecular hydrogen bonding.