O-(6-amino-6-deoxy-α-D-glucopyranosyl)-(1->4)-O-(α-D-glucopyranosyl)-(1->4)-α/β-D-glucopyranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(6-amino-6-deoxy-α-D-glucopyranosyl)-(1->4)-O-(α-D-glucopyranosyl)-(1->4)-α/β-D-glucopyranose
• 英文别名: 6''-amino-6''-deoxymaltotriose；Glc6N(a1-4)Glc(a1-4)Glc；(2R,3S,4S,5R,6R)-2-(aminomethyl)-6-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-3-yl]oxyoxane-3,4,5-triol
• 化学式: C₁₈H₃₃NO₁₅
• 分子量: 503.458
• InChiKey: LHQSSBYNKXFJEU-DZOUCCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7.1
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  275
• 氢给体数：
  11
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  麦芽糖 在 palladium on activated charcoal sodium hydroxide 、 sodium azide 、 cyclodextrin glycosyltransferase 、 human salivary amylase 、 PIPES buffer 、 氢气 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 57.0h， 生成 O-(6-amino-6-deoxy-α-D-glucopyranosyl)-(1->4)-O-(α-D-glucopyranosyl)-(1->4)-α/β-D-glucopyranose
  参考文献：
  名称：

  New enzymatic synthesis of 63-modified maltooligosaccharides and their inhibitory activities for human α-amylases

  摘要：

  Ten new 6(3)-modified maltopentaoses and tetraoses were synthesized by enzymatic reactions utilizing cyclodextrin glycosyltransferase (EC 2.4.1.19) and subsequent human salivary alpha-amylase (HSA) (EC 3.2.1.1). Among these compounds, alpha-D-glucopyranosyl-(1-->4)-alpha-D-glucopyranosyl-(1 -->4)-(6-deoxy-alpha-D-glucopyranosyl)-(1-->4)-alpha-D-glucopyranosyl-(1-->4)-D-glucopyranose (11) and alpha-D-glucopyranosyl-(1--->4)-(6-deoxy-alpha-D-glucopyranosyl)-(1-->4)-alpha-D-glucopyranosyl-(1-->4)-D-glucopyranose (12) showed strong inhibitory activities for human pancreatic alpha-amylase (HPA) and HSA. The IC50 Of 6(3)-deoxymaltopentaose 11 (8.0x10(-5)M for HPA, 1.0x10(-4)M for HSA) and 6(3)-deoxymaltotetraose 12 (2.0x10(-3)M for HPA, 2.0x10(-3)M for HSA) were lower than that of 6(3)-deoxymaltotriose [(6-deoxy-alpha-D-glucopyranosyl)-(1-->4)-alpha-D-glucopyranosyl-(1-->4)-D-glucopyranose 13; 2.0x10-3M for HPA, 4.2x10(-2)M for HSA]. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00029-9

文献信息

• Strong competitive inhibition of porcine pancreaticalpha-amylase by aminodeoxy derivatives of maltose and maltotriose
  作者：Jochen Lehmann、Markus Schmidt-Schuchardt、Jürgen Steck

  DOI：10.1016/s0008-6215(92)84241-j

  日期：1992.12

  The syntheses are described of 6-amino-6-deoxymaltose (2), the 6-amino-6-deoxy (4), 6'-amino-6'-deoxy (6), and 6''-amino-6''-deoxy (8) derivatives of maltotriose, and the methyl alpha- (10) and beta-glycoside (12) and the 1-deoxy derivative (16) of 4. The K(i) values (muM) of these competitive inhibitors of porcine pancreatic alpha-amylase were: 2, 88; 4, 1.9; 6, 2.0; 8, 175; 10, 360; 12, 9000; 16, 7600 (cf. 1800 for maltotriose and 3000 for methyl alpha-maltotrioside). The low values for 4 and 6 reflect reinforcement of the normal binding by ionic attraction and possibly, interaction of the reducing end groups with the protein.
• New enzymatic synthesis of 63-modified maltooligosaccharides and their inhibitory activities for human α-amylases
  作者：Riichiro Uchida、Ayako Nasu、Shoichi Tokutake、Kouichi Kasai、Koichiro Tobe、Nobuyuki Yamaji

  DOI：10.1016/s0008-6215(98)00029-9

  日期：1998.2

  Ten new 6(3)-modified maltopentaoses and tetraoses were synthesized by enzymatic reactions utilizing cyclodextrin glycosyltransferase (EC 2.4.1.19) and subsequent human salivary alpha-amylase (HSA) (EC 3.2.1.1). Among these compounds, alpha-D-glucopyranosyl-(1-->4)-alpha-D-glucopyranosyl-(1 -->4)-(6-deoxy-alpha-D-glucopyranosyl)-(1-->4)-alpha-D-glucopyranosyl-(1-->4)-D-glucopyranose (11) and alpha-D-glucopyranosyl-(1--->4)-(6-deoxy-alpha-D-glucopyranosyl)-(1-->4)-alpha-D-glucopyranosyl-(1-->4)-D-glucopyranose (12) showed strong inhibitory activities for human pancreatic alpha-amylase (HPA) and HSA. The IC50 Of 6(3)-deoxymaltopentaose 11 (8.0x10(-5)M for HPA, 1.0x10(-4)M for HSA) and 6(3)-deoxymaltotetraose 12 (2.0x10(-3)M for HPA, 2.0x10(-3)M for HSA) were lower than that of 6(3)-deoxymaltotriose [(6-deoxy-alpha-D-glucopyranosyl)-(1-->4)-alpha-D-glucopyranosyl-(1-->4)-D-glucopyranose 13; 2.0x10-3M for HPA, 4.2x10(-2)M for HSA]. (C) 1998 Elsevier Science Ltd. All rights reserved.