1-amino-2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-glycero-D-ido-heptitol | 103977-05-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-amino-2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-glycero-D-ido-heptitol
• 英文别名: (2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)methyl amine
• CAS: 103977-05-5
• 化学式: C₃₅H₃₉NO₅
• 分子量: 553.698
• InChiKey: BMSCNMNZBFNHHB-CKQPALCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.69
• 重原子数：
  41.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  72.17
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-amino-2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-glycero-D-ido-heptitol 在 lithium aluminium tetrahydride 、 二苯基膦叠氮化物 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-1-[(1-oxopentyl-5-hydroxy)amino]-D-glycero-D-ido-heptitol
  参考文献：
  名称：

  Recognition Properties of Processing α‐Glucosidase I and α‐Glucosidase II

  摘要：

  All four possible monodeoxy derivatives of p-nitrophenyl alpha-D-glucopyranoside (PNP Glc) and 1-amino-2,6-anhydro-1-deOXY-D-glycero-D-ido-heptitol derivatives were prepared and used as substrates and inhibitors of rat liver processing alpha-glucosidases. alpha-Glucosidase II hydrolyzed the 2-deoxy derivative of PNP Glc (1); the hydrolysis of 1 was more rapid than that of PNP Glc. These results indicate that the presence of a C-2 hydroxyl group is not essential for the action of alpha-glucosidase II. In contrast, PNP Glc and all of the deoxy derivatives of PNP Glc 1-4 inhibited alpha-glucosidase I. These results indicate that alpha-glucosidase I does not necessarily need all of the hydroxyl groups of the glycon moiety for binding to the enzyme. 2,6-Anhydro-1-benzamide-D-glycero-D-ido-heptitol (11), with a terminal phenyl group, inhibited a-glucosidase I and a-glucosidase II. Both alpha-glucosidase I and II showed the same aglycon specificities. When probes 5-12 were assayed for their ability to inhibit processing by a-glucosidases at the cellular level, no effects on glycoprotein processing were observed.

  DOI：

  10.1081/car-120030022
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl cyanide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以94.4%的产率得到1-amino-2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-glycero-D-ido-heptitol
  参考文献：
  名称：

  Recognition Properties of Processing α‐Glucosidase I and α‐Glucosidase II

  摘要：

  All four possible monodeoxy derivatives of p-nitrophenyl alpha-D-glucopyranoside (PNP Glc) and 1-amino-2,6-anhydro-1-deOXY-D-glycero-D-ido-heptitol derivatives were prepared and used as substrates and inhibitors of rat liver processing alpha-glucosidases. alpha-Glucosidase II hydrolyzed the 2-deoxy derivative of PNP Glc (1); the hydrolysis of 1 was more rapid than that of PNP Glc. These results indicate that the presence of a C-2 hydroxyl group is not essential for the action of alpha-glucosidase II. In contrast, PNP Glc and all of the deoxy derivatives of PNP Glc 1-4 inhibited alpha-glucosidase I. These results indicate that alpha-glucosidase I does not necessarily need all of the hydroxyl groups of the glycon moiety for binding to the enzyme. 2,6-Anhydro-1-benzamide-D-glycero-D-ido-heptitol (11), with a terminal phenyl group, inhibited a-glucosidase I and a-glucosidase II. Both alpha-glucosidase I and II showed the same aglycon specificities. When probes 5-12 were assayed for their ability to inhibit processing by a-glucosidases at the cellular level, no effects on glycoprotein processing were observed.

  DOI：

  10.1081/car-120030022

文献信息

• Synthesis of thiourea-tethered C-glycosyl amino acids via isothiocyanate–amine coupling
  作者：Reham F. Barghash、Alessandro Massi、Alessandro Dondoni

  DOI：10.1039/b908156a

  日期：——

  A new class of C-glycosyl amino acids displaying a thiourea segment as a linker has been designed and synthesized by addition of peracetylated glycosylmethyl isothiocyanates to an amine-functionalized amino acid (Nα-Fmoc-β-amino-L-alanine). Three pairs of compounds with α- and β-galacto, α- and β-gluco, and α- and β-manno configuration have been prepared with yields ranging between 70 and 75%. The orthogonal set of protective groups (O-acetyl in the carbohydrate moiety and N-Fmoc in the amino acid residue) makes these compounds suitable substrates for the co-translational modification of natural peptides. The couplings of model hydroxy-free and perbenzylated glycosylmethyl isothiocyanates with the above Nα-Fmoc-β-amino-L-alanine and the Nα-Boc-protected analogue have been carried out as well, thus broadening the scope of the coupling reaction. Nevertheless, there are limitations of this isothiocyanate–amine coupling in complex systems, and these are briefly discussed.

  通过将乙酰化的糖基甲基异硫氰酸酯添加到胺功能化的氨基酸（Nα-Fmoc-β-氨基-L-丙氨酸）上，设计并合成了一类新的具有硫脲键段的C-糖基氨基酸。制备了三种分别具有α-和β-半乳糖、α-和β-葡萄糖以及α-和β-甘露糖构型的化合物，产率在70%至75%之间。保护基团（糖部分中的O-乙酰基和氨基酸残基中的N-Fmoc）的正交性使得这些化合物适合作为天然肽共翻译修饰的底物。还进行了模型无羟基和苯甲酰化的糖基甲基异硫氰酸酯与上述Nα-Fmoc-β-氨基-L-丙氨酸及其Nα-Boc保护类似物的偶联反应，从而扩大了偶联反应的范围。然而，这种异硫氰酸酯-胺偶联在复杂系统中存在局限性，这些局限性在此简要讨论。
• Fernandez-Resa; Garcia-Lopez; De Las Heras, European Journal of Medicinal Chemistry, 1986, vol. 21, # 3, p. 245 - 249
  作者：Fernandez-Resa、Garcia-Lopez、De Las Heras、et al.

  DOI：——

  日期：——