O-α-D-Glucopyranosyl-(1-3)-α,β-L-rhamnopyranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-α-D-Glucopyranosyl-(1-3)-α,β-L-rhamnopyranose
• 英文别名: β-D-glucopyranosyl-L-rhamnose；3-O-alpha-D-glucopyranosyl-L-rhamnopyranose；(3R,4R,5S,6S)-6-methyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2,3,5-triol
• 化学式: C₁₂H₂₂O₁₀
• 分子量: 326.301
• InChiKey: QOVCLNNAYZUHEK-NYVVRXGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  169
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  O-α-D-Glucopyranosyl-(1-3)-α,β-L-rhamnopyranose 、 H3PO4 生成 β-D-glucose 1-phosphate 、 L-rhamnopyranose
  参考文献：
  名称：

  3-O-α-d-Glucopyranosyl-l-rhamnose phosphorylase from Clostridium phytofermentans

  摘要：

  We found an unreported activity of phosphorylase catalyzed by a protein (Cphy1019) belonging to glycoside hydrolase family 65 (GH65) from Clostridium phytofermentans. The recombinant Cphy1019 produced in Escherichia coli did not phosphorolyze alpha-linked glucobioses, such as trehalose (alpha 1-alpha 1), kojibiose (alpha 1-2), nigerose (alpha 1-3), and maltose (alpha 1-4), which are typical substrates for GH65 enzymes. In reverse phosphorolysis, Cphy1019 utilized only L-rhamnose as the acceptor among various sugars examined with beta-D-glucose 1-phosphate as the donor. The reaction product was determined to be 3-O-alpha-D-glucopyranosyl-L-rhamnose, indicating strict alpha 1-3 regioselectivity. We propose 3-O-alpha-D-glucopyranosyl-L-rhamnose: phosphate beta-D-glucosyltransferase as the systematic name and 3-O-alpha-D-glucopyranosyl-L-rhamnose phosphorylase as the short name for this novel GH65 phosphorylase. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.12.019
• 作为产物：
  描述：

  Benzyl 2,4-di-O-benzyl-α-L-rhamnopyranoside 在 palladium on activated charcoal 盐酸 、 4 A molecular sieve 、 potassium tert-butylate 、 氢气 、 三氟甲烷磺酸甲酯 作用下， 以 乙醚 、 乙醇 为溶剂， 90.0 ℃ 、392.24 kPa 条件下， 反应 1.5h， 生成 O-α-D-Glucopyranosyl-(1-3)-α,β-L-rhamnopyranose
  参考文献：
  名称：

  肺炎链球菌6A和6B型荚膜多糖结构成分的合成

  摘要：

  O-alpha-d-Glucopyranosyl-（1 ---- 3）-alpha，beta-L-鼠李吡喃糖（15），O-alpha-D-吡喃半乳糖基-（1 ---- 3）-O-alpha-D -吡喃葡萄糖基-（1 ---- 3）-α-α，β-L-鼠李糖吡喃糖（17），O-α-D-吡喃吡喃糖基-（1 ---- 3）-O-α-D-吡喃葡糖基-（ 1 ---- 3）-O-α-L-鼠李吡喃糖基-（1 ---- 3）-D-核糖醇（23）和O-α-D-半乳糖吡喃糖基-（1 ---- 3）- O-α-D-吡喃葡萄糖基-（1 ---- 3）-O-α-L-鼠李糖基吡喃糖基-（1 ---- 4）-D-核糖醇（27），它们是荚膜多糖的结构成分肺炎链球菌6A和6B型（[---- 2] -alpha-D-Galp-（1 ---- 3）-alpha-D-Glcp-（1 ---- 3）-alpha-L-Rhap -已经合成了-（1

  DOI：

  10.1016/0008-6215(90)84051-u

文献信息

• 3-O-α-d-Glucopyranosyl-l-rhamnose phosphorylase from Clostridium phytofermentans
  作者：Takanori Nihira、Hiroyuki Nakai、Motomitsu Kitaoka

  DOI：10.1016/j.carres.2011.12.019

  日期：2012.3

  We found an unreported activity of phosphorylase catalyzed by a protein (Cphy1019) belonging to glycoside hydrolase family 65 (GH65) from Clostridium phytofermentans. The recombinant Cphy1019 produced in Escherichia coli did not phosphorolyze alpha-linked glucobioses, such as trehalose (alpha 1-alpha 1), kojibiose (alpha 1-2), nigerose (alpha 1-3), and maltose (alpha 1-4), which are typical substrates for GH65 enzymes. In reverse phosphorolysis, Cphy1019 utilized only L-rhamnose as the acceptor among various sugars examined with beta-D-glucose 1-phosphate as the donor. The reaction product was determined to be 3-O-alpha-D-glucopyranosyl-L-rhamnose, indicating strict alpha 1-3 regioselectivity. We propose 3-O-alpha-D-glucopyranosyl-L-rhamnose: phosphate beta-D-glucosyltransferase as the systematic name and 3-O-alpha-D-glucopyranosyl-L-rhamnose phosphorylase as the short name for this novel GH65 phosphorylase. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of structural elements of the capsular polysaccharides of Streptococcus pneumoniae types 6A and 6B
  作者：Ted M. Slaghek、Anita H. van Oijen、Augustinus A.M. Maas、Johannis P. Kamerling、Johannes F.G. Vliegenthart

  DOI：10.1016/0008-6215(90)84051-u

  日期：1990.10

  copyranosyl-(1----3)- O-alpha-L-rhamnopyranosyl-(1----4)-D-ribitol (27), which are structural elements of the capsular polysaccharides of Streptococcus pneumoniae types 6A and 6B ([----2)-alpha-D-Galp-(1----3)-alpha-D-Glcp-(1----3)-alpha-L-Rhap- (1----X)- D-Rib-ol-(5-P----]n; 6A X = 3, 6B X = 4), have been synthesised. Ethyl 3-O-allyl-2,4,6-tri-O-benzyl-1-thio-beta-D-glucopyranoside (3) was coupled

  O-alpha-d-Glucopyranosyl-（1 ---- 3）-alpha，beta-L-鼠李吡喃糖（15），O-alpha-D-吡喃半乳糖基-（1 ---- 3）-O-alpha-D -吡喃葡萄糖基-（1 ---- 3）-α-α，β-L-鼠李糖吡喃糖（17），O-α-D-吡喃吡喃糖基-（1 ---- 3）-O-α-D-吡喃葡糖基-（ 1 ---- 3）-O-α-L-鼠李吡喃糖基-（1 ---- 3）-D-核糖醇（23）和O-α-D-半乳糖吡喃糖基-（1 ---- 3）- O-α-D-吡喃葡萄糖基-（1 ---- 3）-O-α-L-鼠李糖基吡喃糖基-（1 ---- 4）-D-核糖醇（27），它们是荚膜多糖的结构成分肺炎链球菌6A和6B型（[---- 2] -alpha-D-Galp-（1 ---- 3）-alpha-D-Glcp-（1 ---- 3）-alpha-L-Rhap -已经合成了-（1