N-boc-(4-aminobutyl)biotinamide | 1001575-89-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 英文名称: N-boc-(4-aminobutyl)biotinamide
• 英文别名: {4-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-butyl}-carbamic acid tert-butyl ester；N-Biotinyl-N'-Boc-1,4-butanediamine；tert-butyl N-[4-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]butyl]carbamate
• CAS: 1001575-89-8
• 化学式: C₁₉H₃₄N₄O₄S
• 分子量: 414.569
• InChiKey: FHYIVBSOJVLBKD-DZKIICNBSA-N

物化性质

• 熔点：
  178-180 °C
• 沸点：
  709.8±55.0 °C(Predicted)
• 密度：
  1.136±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  N-boc-(4-aminobutyl)biotinamide 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.5h， 生成 (S)-5,5,5-trifluoro-4-(N-(4-fluorobenzyl)-2-((R)-5-(3-methylureido)-2',4'-dioxo-2,3-dihydrospiro[indene-1,5'-oxazolidin]-3'-yl)acetamido)-N-(4-(5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)butyl)pentanamide
  参考文献：
  名称：

  Identification of ligand linkage vectors for the development of p300/CBP degraders

  摘要：

  为了从现有的蛋白质配体中开发新的退化分子，必须确定连接向量，然后将其与适当的E3连接酶结合，而不会破坏与相应靶标的结合。

  DOI：

  10.1039/d1md00070e
• 作为产物：
  描述：

  N-叔丁氧羰基-1,4-丁二胺 、 五氟苯酚生物素酯 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以85%的产率得到N-boc-(4-aminobutyl)biotinamide
  参考文献：
  名称：

  Identification of ligand linkage vectors for the development of p300/CBP degraders

  摘要：

  为了从现有的蛋白质配体中开发新的退化分子，必须确定连接向量，然后将其与适当的E3连接酶结合，而不会破坏与相应靶标的结合。

  DOI：

  10.1039/d1md00070e

文献信息

• Design, Synthesis, and Immunological Evaluation of a Multicomponent Construct Based on a Glycotripeptoid Core Comprising B and T Cell Epitopes and a Toll-like Receptor 7 Agonist That Elicits Potent Immune Responses
  作者：Thomas Szekely、Olivier Roy、Edith Dériaud、Aurélie Job、Richard Lo-Man、Claude Leclerc、Claude Taillefumier

  DOI：10.1021/acs.jmedchem.8b00960

  日期：2018.11.8

  We present here for the first time the synthesis and immunological evaluation of a fully synthetic three-component anticancer vaccine candidate that consists of a β-glycotripeptoid core mimicking a cluster of Tn at the surface of tumor cells (B epitope), conjugated to the OVA 323–339 peptide (T-cell epitope) and a Toll-like receptor 7 (TLR7) agonist for potent adjuvanticity. The immunological evaluation

  我们在此首次提出完全合成的三组分抗癌疫苗候选物的合成和免疫学评估，该候选物由与OVA缀合的模仿肿瘤细胞表面的Tn簇（B表位）的β-糖三肽核心构成323–339肽（T细胞表位）和Toll样受体7（TLR7）激动剂，具有较强的佐剂作用。对该构建体和前体组分的免疫学评估证明了缀合物中各组分对刺激先天性和适应性免疫细胞（DC，T辅助细胞和B细胞）的协同活性。出乎意料的是，用基于三组分GalNAc的构建体免疫小鼠引起低水平的抗Tn IgG，但是引起非常高水平的识别TLR7激动剂的抗体。
• Synthesis and structural characterization of carboxyethylpyrrole-modified proteins: mediators of age-related macular degeneration
  作者：Liang Lu、Xiaorong Gu、Li Hong、James Laird、Keeve Jaffe、Jaewoo Choi、John Crabb、Robert G. Salomon

  DOI：10.1016/j.bmc.2009.09.009

  日期：2009.11

  Protein modifications in which the e-amino group of lysyl residues is incorporated into a 2-(omega-carboxy-ethyl)pyrrole (CEP) are mediators of age-related macular degeneration (AMD). They promote both angiogenesis into the retina ('wet AMD') and geographic retinal atrophy ('dry AMD'). Blood levels of CEPs are biomarkers for clinical prognosis of the disease. To enable mechanistic studies of their role in promoting AMD, for example, through the activation of B- and T-cells, interaction with receptors, or binding with complement proteins, we developed an efficient synthesis of CEP derivatives, that is especially effective for proteins. The structures of tryptic peptides derived from CEP-modified proteins were also determined. A key finding is that 4,7-dioxoheptanoic acid 9-fluorenylmethyl ester reacts with primary amines to provide 9-fluorenylmethyl esters of CEP-modified proteins that can be deprotected in situ with 1,8-diazabicyclo[5.4.0]undec-7-ene without causing protein denaturation. The introduction of multiple CEP-modifications with a wide variety of CEP: protein ratios is readily achieved using this strategy. (C) 2009 Elsevier Ltd. All rights reserved.