1-(N-t-BOC-amino)-6-hemisuccinamidohexane | 157801-09-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-(N-t-BOC-amino)-6-hemisuccinamidohexane
• 英文别名: HO2C(CH2)2C(O)NH(CH2)6NHBoc；4-[6-[(2-Methylpropan-2-yl)oxycarbonylamino]hexylamino]-4-oxobutanoic acid
• CAS: 157801-09-7
• 化学式: C₁₅H₂₈N₂O₅
• 分子量: 316.398
• InChiKey: VSPPCGSCNGWZTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  1-(N-t-BOC-amino)-6-hemisuccinamidohexane 在 盐酸 、 甲酸 、 β-烟酰胺单核苷酸 、 氯甲酸异丁酯 作用下， 以 乙酸乙酯 为溶剂， 反应 5.25h， 生成 p-nitrophenyl N-<<(6-aminohexyl)succinamido>-L-alanyl-L-alanyl-L-prolylmethyl>-N-isopropylcarbamate hydrochloride
  参考文献：
  名称：

  Synthetic Macromolecular Inhibitors of Human Leukocyte Elastase. 1. Synthesis of Peptidyl Carbamates Bound to Water-Soluble Polymers: Poly-.alpha.,.beta.-[N-(2-hydroxyethyl)-D,L-aspartamide] and Poly-.alpha.-[N5-(2-hydroxyethyl)-L-glutamine]

  摘要：

  The design and synthesis of macromolecular peptidyl carbamate inhibitors of human leukocyte elastase (HLE), based on coupling of a low-molecular-weight peptidyl carbamate, succinylalanylalanylprolylmethyl isopropyl carbamate, with a linear hydrophilic polymer, poly-alpha,beta-[N-(2-hydroxyethyl)-D,L-aspartamide] or poly-alpha-[N-5-(2-hydroxyethyl)-L-glutamine], is described. The covalent linkage between a flexible linear polymer and a peptidyl carbamate inhibitor of HLE did not compromise in vitro inhibitory capacity. The macromolecular peptidyl carbamates reported here represent a novel class of elastase inhibitors with a K-i ranging from 35.5 to 2.0 nM.

  DOI：

  10.1021/jm00038a014
• 作为产物：
  描述：

  丁二酸酐 、 N-BOC-1,6-己二胺盐酸盐 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以74%的产率得到1-(N-t-BOC-amino)-6-hemisuccinamidohexane
  参考文献：
  名称：

  Synthetic Macromolecular Inhibitors of Human Leukocyte Elastase. 1. Synthesis of Peptidyl Carbamates Bound to Water-Soluble Polymers: Poly-.alpha.,.beta.-[N-(2-hydroxyethyl)-D,L-aspartamide] and Poly-.alpha.-[N5-(2-hydroxyethyl)-L-glutamine]

  摘要：

  The design and synthesis of macromolecular peptidyl carbamate inhibitors of human leukocyte elastase (HLE), based on coupling of a low-molecular-weight peptidyl carbamate, succinylalanylalanylprolylmethyl isopropyl carbamate, with a linear hydrophilic polymer, poly-alpha,beta-[N-(2-hydroxyethyl)-D,L-aspartamide] or poly-alpha-[N-5-(2-hydroxyethyl)-L-glutamine], is described. The covalent linkage between a flexible linear polymer and a peptidyl carbamate inhibitor of HLE did not compromise in vitro inhibitory capacity. The macromolecular peptidyl carbamates reported here represent a novel class of elastase inhibitors with a K-i ranging from 35.5 to 2.0 nM.

  DOI：

  10.1021/jm00038a014

文献信息

• Adaptable Synthesis of <i>C</i>-Glycosidic Multivalent Carbohydrates and Succinamide-Linked Derivatization
  作者：Gavin J. Miller、John M. Gardiner

  DOI：10.1021/ol102310x

  日期：2010.11.19

  A modular approach to the synthesis of trivalent C-glycosidic carbohydrates is described. The approach is illustrated employing carboxylate-terminated C-glycosidic D-mannose, D-glucose, and D-galactose derivatives with different length C1-linked spacer units and also core units with different length linker units attached. The central core scaffold is additionally functionalized via a succinamide-based, conjugatable linker unit, exemplified in an extended multivalent derivative [31] and a pyrene-bearing fluorsecent-labeled tris-C-mannosyl conjugate [33].
• Synthetic Macromolecular Inhibitors of Human Leukocyte Elastase. 1. Synthesis of Peptidyl Carbamates Bound to Water-Soluble Polymers: Poly-.alpha.,.beta.-[N-(2-hydroxyethyl)-D,L-aspartamide] and Poly-.alpha.-[N5-(2-hydroxyethyl)-L-glutamine]
  作者：Frantisek Rypacek、William R. Banks、Dagmar Noskova、George A. Digenis

  DOI：10.1021/jm00038a014

  日期：1994.6

  The design and synthesis of macromolecular peptidyl carbamate inhibitors of human leukocyte elastase (HLE), based on coupling of a low-molecular-weight peptidyl carbamate, succinylalanylalanylprolylmethyl isopropyl carbamate, with a linear hydrophilic polymer, poly-alpha,beta-[N-(2-hydroxyethyl)-D,L-aspartamide] or poly-alpha-[N-5-(2-hydroxyethyl)-L-glutamine], is described. The covalent linkage between a flexible linear polymer and a peptidyl carbamate inhibitor of HLE did not compromise in vitro inhibitory capacity. The macromolecular peptidyl carbamates reported here represent a novel class of elastase inhibitors with a K-i ranging from 35.5 to 2.0 nM.