(S)-2,6-Bis-benzyloxycarbonylamino-hexanoic acid (2R,3S,5R)-5-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester | 173410-91-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: (S)-2,6-Bis-benzyloxycarbonylamino-hexanoic acid (2R,3S,5R)-5-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester
• CAS: 173410-91-8
• 化学式: C₃₂H₃₇N₇O₉
• 分子量: 663.687
• InChiKey: YRAGPOOHUHEWJP-CXSMSNRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.29
• 重原子数：
  48.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  222.01
• 氢给体数：
  5.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  (S)-2,6-Bis-benzyloxycarbonylamino-hexanoic acid (2R,3S,5R)-5-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以38%的产率得到[(2R,3S,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methyl (2S)-2,6-diaminohexanoate
  参考文献：
  名称：

  Chemical Aspects of the Benzophenone-Photosensitized Formation of Two Lysine-2'-deoxyguanosine Cross-Links

  摘要：

  1-lysine, 5'-ester with 2'-deoxyguanosine (5'-Lys-dGuo), has been synthesized in order to investigate the photosensitized formation of lysine-2'aeoxyguanosine (lysine-dGuo) adducts. The purpose of tethering a lysine residue to the S-hydroxyl group of dGuo was to mimic the close interaction between DNA and amino acids of histones within cells. Benzophenone-mediated photosensitization of 5'-Lys-dGuo in aerated aqueous solution was found to give rise to two main intramolecular adducts involving the a-amino function of the lysine residue and the C8 position of the guanine moiety. The two modified nucleosides were isolated by reversed-phase high-performance liquid chromatography and characterized by extensive spectroscopic measurements including C-13 and H-1 NMR analyses together with fast atom bombardment mass spectroscopy (FAB-MS). They were identified as L-lysine, N-2-[5[(aminoiminomethyl)imino]-1-(2-deoxy-beta-D-erythro-pentofuranosyl)-4-oxoimidazolidmyl]-, intramolecular 1,5/-ester (6) and L-lysine, N-2-[1-(2-deoxy-beta-D-erythro-pentofuranosyl)-4,5-dihydro-4,5-dioxo-1H-imidazol-2-yl]-, intramolecular 1,5'-ester (10). The structure assignment of the two photoadducts is indicative of the occurrence of two mechanisms. One is Likely to involve a nucleophilic substitution of the guanine radical cation by the a-amino group of the lysine residue. On the other hand, the formation of 6 may be explained in terms of an intramolecular addition of the cl-amino function to the 7,8-double bond of a neutral guanine radical.

  DOI：

  10.1021/ja00155a005
• 作为产物：
  描述：

  N,N’-双苄氧羰基-L-赖氨酸 、 2'-脱氧鸟苷 在 三正丁胺 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以26%的产率得到(S)-2,6-Bis-benzyloxycarbonylamino-hexanoic acid (2R,3S,5R)-5-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester
  参考文献：
  名称：

  Chemical Aspects of the Benzophenone-Photosensitized Formation of Two Lysine-2'-deoxyguanosine Cross-Links

  摘要：

  1-lysine, 5'-ester with 2'-deoxyguanosine (5'-Lys-dGuo), has been synthesized in order to investigate the photosensitized formation of lysine-2'aeoxyguanosine (lysine-dGuo) adducts. The purpose of tethering a lysine residue to the S-hydroxyl group of dGuo was to mimic the close interaction between DNA and amino acids of histones within cells. Benzophenone-mediated photosensitization of 5'-Lys-dGuo in aerated aqueous solution was found to give rise to two main intramolecular adducts involving the a-amino function of the lysine residue and the C8 position of the guanine moiety. The two modified nucleosides were isolated by reversed-phase high-performance liquid chromatography and characterized by extensive spectroscopic measurements including C-13 and H-1 NMR analyses together with fast atom bombardment mass spectroscopy (FAB-MS). They were identified as L-lysine, N-2-[5[(aminoiminomethyl)imino]-1-(2-deoxy-beta-D-erythro-pentofuranosyl)-4-oxoimidazolidmyl]-, intramolecular 1,5/-ester (6) and L-lysine, N-2-[1-(2-deoxy-beta-D-erythro-pentofuranosyl)-4,5-dihydro-4,5-dioxo-1H-imidazol-2-yl]-, intramolecular 1,5'-ester (10). The structure assignment of the two photoadducts is indicative of the occurrence of two mechanisms. One is Likely to involve a nucleophilic substitution of the guanine radical cation by the a-amino group of the lysine residue. On the other hand, the formation of 6 may be explained in terms of an intramolecular addition of the cl-amino function to the 7,8-double bond of a neutral guanine radical.

  DOI：

  10.1021/ja00155a005