(S)-N-[(tert-butoxy)carbonyl]-γ-(guanin-9-yl)-β-homoalanine | 517877-42-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: (S)-N-[(tert-butoxy)carbonyl]-γ-(guanin-9-yl)-β-homoalanine
• 英文别名: Boc-β-HalG-OH；(S)-4-(2-Amino-6-oxo-3H-purin-9(6H)-yl)-3-((tert-butoxycarbonyl)amino)butanoic acid；(3S)-4-(2-amino-6-oxo-1H-purin-9-yl)-3-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid
• CAS: 517877-42-8
• 化学式: C₁₄H₂₀N₆O₅
• 分子量: 352.35
• InChiKey: XQAUGJDRQJJTRS-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  161
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-N-[(tert-butoxy)carbonyl]-γ-(guanin-9-yl)-β-homoalanine 、 (S)-N-[(tert-butoxy)carbonyl]-γ-[N⁴-(benzyloxycarbonyl)cytosin-1-yl]-β-homoalanine 生成 H-(S)-γ-(guanin-9-yl)-β-homoalaninyl-(S)-γ-(cytosin-9-yl)-β-homoalaninyl-(S)-γ-(guanin-9-yl)-β-homoalaninyl-(S)-γ-(cytosin-9-yl)-β-homoalaninyl-(S)-γ-(guanin-9-yl)-β-homoalaninyl-(S)-γ-(cytosin-9-yl)-β-homoalaninyl-D-lysine amide
  参考文献：
  名称：

  Nucleo--Amino Acids: Synthesis and Oligomerization to -Homoalanyl-PNA

  摘要：

  The synthesis of thyminyl-, uracilyl-, cytosinyl-, and guaninyl-beta(3)-amino acids and the oligomerization of the cytosinyl- and guaninyl-beta(3)-amino acids to beta-homoalanyl-PNA are presented. The pyrimidinyl nucleobases were connected to the gamma-position of beta-homoalanine by Mitsunobu reaction with a beta-homoserine derivative or by nucleophilic substitution of methanesulfonates. For the preparation of the guaninyl-beta(3)-amino acid, a beta-lactam route was established that might be of interest also for the synthesis of other beta(3)-amino acid derivatives. The cytosinyl and guaninyl building blocks were oligomerized to hexamers. They form quite stable self-pairing complexes in H2O as indicated by temperature dependent UV and CD spectroscopy.

  DOI：

  10.1002/1522-2675(200211)85:11<3855::aid-hlca3855>3.0.co;2-a
• 作为产物：
  描述：

  benzyl (3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoate 在 sodium hydroxide 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 284.0h， 生成 (S)-N-[(tert-butoxy)carbonyl]-γ-(guanin-9-yl)-β-homoalanine
  参考文献：
  名称：

  Nucleo--Amino Acids: Synthesis and Oligomerization to -Homoalanyl-PNA

  摘要：

  The synthesis of thyminyl-, uracilyl-, cytosinyl-, and guaninyl-beta(3)-amino acids and the oligomerization of the cytosinyl- and guaninyl-beta(3)-amino acids to beta-homoalanyl-PNA are presented. The pyrimidinyl nucleobases were connected to the gamma-position of beta-homoalanine by Mitsunobu reaction with a beta-homoserine derivative or by nucleophilic substitution of methanesulfonates. For the preparation of the guaninyl-beta(3)-amino acid, a beta-lactam route was established that might be of interest also for the synthesis of other beta(3)-amino acid derivatives. The cytosinyl and guaninyl building blocks were oligomerized to hexamers. They form quite stable self-pairing complexes in H2O as indicated by temperature dependent UV and CD spectroscopy.

  DOI：

  10.1002/1522-2675(200211)85:11<3855::aid-hlca3855>3.0.co;2-a

文献信息

• Synthesis of a 7-Deazaguanine-Functionalized β-Amino Acid: Improved Specificity of β-Peptide Helix Organization
  作者：Pradip Chakraborty、Arndt M. Brückner、Ulf Diederichsen

  DOI：10.1002/ejoc.200501003

  日期：2006.5

  Nucleobase-functionalized β-peptides are a suitable scaffold for the construction of well-defined tertiary structures organized by nucleobase pair recognition. Since guanine-rich oligomers are especially known to form higher aggregates, an enantiomerically pure 7-deazaguanine (zG)-functionalized nucleo-β3-amino acid was synthesized from a β-lactam derivative as a key intermediate. Incorporated into

  核碱基功能化的 β-肽是构建由核碱基对识别组织的明确三级结构的合适支架。由于富含鸟嘌呤的低聚物尤其会形成更高的聚集体，因此从作为关键中间体的 β-内酰胺衍生物合成了对映异构纯的 7-脱氮鸟嘌呤 (zG) 功能化的核-β3-氨基酸。结合到 β-肽 14-螺旋中，可以减少聚集现象并提高识别选择性。碱基对介导的螺旋识别的证据是通过温度依赖性 UV 和 CD 光谱获得的。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Uniformly Nucleobase-Functionalized β-Peptide Helices: Watson–Crick Pairing or Nonspecific Aggregation
  作者：Angelina Weiß、Ulf Diederichsen

  DOI：10.1002/ejoc.200700444

  日期：2007.11

  organization and architecture of helices is fundamental in folding of protein tertiary structures. Therefore, stable β-peptide helices are used as models for the selective organization of secondary structures. Nucleobases are already established as recognition elements to organize two β-peptide helices in antiparallel orientation. The investigation of β-peptide helices uniformly functionalized with one type

  螺旋的组织和结构是蛋白质三级结构折叠的基础。因此，稳定的β-肽螺旋被用作二级结构选择性组织的模型。核碱基已经被确定为识别元件，以组织两个反平行方向的 β-肽螺旋。对用一种核碱基均匀功能化的 β-肽螺旋的研究提供了对线性和非常刚性的螺旋骨架拓扑结构内特定相互作用的识别模式和要求的进一步了解。一旦允许 Watson-Crick 配对，基于碱基对识别的特定螺旋相互作用就占主导地位。如果氢键供体/受体模式禁止沃森-克里克几何，基于芳香相互作用或非特异性氢键网络，发现了一种非常稳定的非特异性相互作用。酪氨酸侧链也证实了后者的聚集。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005）
• Nucleo--Amino Acids: Synthesis and Oligomerization to -Homoalanyl-PNA
  作者：Arndt M. Brückner、Harald W. Schmitt、Ulf Diederichsen

  DOI：10.1002/1522-2675(200211)85:11<3855::aid-hlca3855>3.0.co;2-a

  日期：2002.11

  The synthesis of thyminyl-, uracilyl-, cytosinyl-, and guaninyl-beta(3)-amino acids and the oligomerization of the cytosinyl- and guaninyl-beta(3)-amino acids to beta-homoalanyl-PNA are presented. The pyrimidinyl nucleobases were connected to the gamma-position of beta-homoalanine by Mitsunobu reaction with a beta-homoserine derivative or by nucleophilic substitution of methanesulfonates. For the preparation of the guaninyl-beta(3)-amino acid, a beta-lactam route was established that might be of interest also for the synthesis of other beta(3)-amino acid derivatives. The cytosinyl and guaninyl building blocks were oligomerized to hexamers. They form quite stable self-pairing complexes in H2O as indicated by temperature dependent UV and CD spectroscopy.