8-[3-[[[2-(乙酰氨基)-2-脱氧-beta-D-吡喃葡糖基]氧基]甲基]-3H-双吖丙啶-3-基]辛基2-(乙酰氨基)-2-脱氧-beta-D-吡喃葡糖苷 | 146294-05-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 8-[3-[[[2-(乙酰氨基)-2-脱氧-beta-D-吡喃葡糖基]氧基]甲基]-3H-双吖丙啶-3-基]辛基2-(乙酰氨基)-2-脱氧-beta-D-吡喃葡糖苷
• 英文名称: 1,10-Di-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-azi-1,10-decanediol
• 英文别名: 1,10-Di-O-(2-acetamido-2-deoxyglucopyranosyl)-2-azi-1,10-decanediol；N-[(2R,3R,4R,5S,6R)-2-[8-[3-[[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]diazirin-3-yl]octoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 146294-05-5
• 化学式: C₂₆H₄₆N₄O₁₂
• 分子量: 606.671
• InChiKey: OCYKVCXQMCPXTQ-YBWAQPBCSA-N

物化性质

• 密度：
  1.54±0.1 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  42
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  241
• 氢给体数：
  8
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  uridine 5'-diphospho-β-D-galactose 、 8-[3-[[[2-(乙酰氨基)-2-脱氧-beta-D-吡喃葡糖基]氧基]甲基]-3H-双吖丙啶-3-基]辛基2-(乙酰氨基)-2-脱氧-beta-D-吡喃葡糖苷 在 Β-1,4-半乳糖基转移酶来源于牛奶 作用下， 以 水 为溶剂， 以28%的产率得到
  参考文献：
  名称：

  A spacer-modified disaccharide as a photoaffinity reagent for the acceptor-binding area of bovine (1 → 4)-β-d-galactosyltransferase: comparison of its acceptor properties with those of other 2-acetamido-2-deoxy-β-d-glucopyranosides

  摘要：

  The spacer-modified disaccharide 1,10-di-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-2-azi-1,10-decanediol (10) that mimics the biantennary. core heptasaccharide of N-glycoproteins has been synthesised. Compound 10 is an excellent acceptor in galactosyltransferase-catalysed galactosylation by UDP-galactose, is superior (7-8-fold) to analogues that have only one GlcNAc unit, and is an efficient photoaffinity reagent for galactosyltransferase. In the presence of UDP-Gal. no photoaffinity labelling by 10 takes place, which agrees the mechanism of galactosyltransferase action.

  DOI：

  10.1016/s0008-6215(00)90925-x
• 作为产物：
  描述：

  1,10-Di-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2-azi-1,10-decanediol 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以93%的产率得到8-[3-[[[2-(乙酰氨基)-2-脱氧-beta-D-吡喃葡糖基]氧基]甲基]-3H-双吖丙啶-3-基]辛基2-(乙酰氨基)-2-脱氧-beta-D-吡喃葡糖苷
  参考文献：
  名称：

  A spacer-modified disaccharide as a photoaffinity reagent for the acceptor-binding area of bovine (1 → 4)-β-d-galactosyltransferase: comparison of its acceptor properties with those of other 2-acetamido-2-deoxy-β-d-glucopyranosides

  摘要：

  The spacer-modified disaccharide 1,10-di-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-2-azi-1,10-decanediol (10) that mimics the biantennary. core heptasaccharide of N-glycoproteins has been synthesised. Compound 10 is an excellent acceptor in galactosyltransferase-catalysed galactosylation by UDP-galactose, is superior (7-8-fold) to analogues that have only one GlcNAc unit, and is an efficient photoaffinity reagent for galactosyltransferase. In the presence of UDP-Gal. no photoaffinity labelling by 10 takes place, which agrees the mechanism of galactosyltransferase action.

  DOI：

  10.1016/s0008-6215(00)90925-x

文献信息

• Spacer-modified trisaccharide glycosides that mimic the biantennary Asn-linked oligosaccharide acceptor of (1 → 4)-β-d-galactosyltransferase and can be used as competitive inhibitors and for irreversible deactivation
  作者：Sándor-Csaba Áts、Jochen Lehmann、Stefan Petry

  DOI：10.1016/s0008-6215(00)90926-1

  日期：1992.9

  The biantennary spacer-modified trisaccharide glycoside methyl 3,6-di-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyloxyethyl)-alpha-D-mannopyranoside (5) was synthesised and used together with several 2-acylamino-2-deoxy-D-glucose derivatives in competition experiments with beta-D-galactosyltransferase. CoMpound 5 was an acceptor substrate (K(M) 0.18 mM) comparable to the biantennary core heptasaccharide of glycoproteins (K(M) 0.13 mM). Replacing the N-acetyl group by other N-acyl groups did not alter the kinetic parameters significantly. When the N-acyl group was iodoacetyl, the compound was an irreversible inhibitor,