1-O-isobutyryl-β-glucopyranose | 151732-11-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-isobutyryl-β-glucopyranose
• 英文别名: glucose isobutyrate；1-O-isobutyryl-beta-D-glucose；[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 2-methylpropanoate
• CAS: 151732-11-5
• 化学式: C₁₀H₁₈O₇
• 分子量: 250.249
• InChiKey: MSYJLYKQOMTGAU-GBMPTNJUSA-N

物化性质

• 沸点：
  405.1±45.0 °C(predicted)
• 密度：
  1.40±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-Deoxy-D-glucose 、 1-O-isobutyryl-β-glucopyranose 在 Lycopersicon pennellii 作用下， 以 various solvent(s) 为溶剂， 反应 6.0h， 生成 1-O-isobutyryl-2-deoxy-β-glucopyranose
  参考文献：
  名称：

  A survey of the nature of glucose acylation reactions in plant extracts

  摘要：

  A variety of plant species have been shown to catalyse anomeric acyl exchange from a number of 1-O-fatty-acyl-beta-glucoses as donor substrates to [(14)C]-glucose as an acceptor. The activity in wild tomato Lycopersicon penneliii has been analysed in detail by using analogs of glucose as accepters and a number of 1-O-acyl-beta-glucoses and 1-O-acyl-2-deoxyglucoses as acyl donors. Compared to 1-O-isobutyryl-beta-glucose, the analogous 1-O-isobutyryl-beta-2-deoxyglucose is an effective donor both to glucose (ca. 75%) and to 2-deoxyglucose (ca. 95%). On the contrary, compared to 1-O-isobutyryl-beta-glucose, 1-O-isobutyryl-alpha-2-deoxyglucose is a poor donor both to glucose (ca. 4%) and to deoxyglucose (ca. 6%). The glucose analogs free at the anomeric center such as 3-O-methylglucose and 2-deoxyglucose are competent acyl accepters from various 1-O-acyl-beta-glucoses whereas 1-O-methylglucose is not. The primary initial product of acyl transfer from 1-O-isobutyryl-beta-glucose to [(14)C]-glucose is beta-glucosidase-cleavable 1-O-acyl-[(14)C]-beta-glucose, whereas the isobutyryl-[(14)C]-3-O-methylglucose generated from 1-O-isobutyryl-beta-glucose and [(14)C]-3-O-methylglucose is beta-glucosidase-resistant. The transfer of the acyl group to 3-O-methylglucose occurs at the anomeric center; therefore the resistance to beta-glucosidase reflects the strict specificity of beta-glucosidase for glucose. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(99)00319-2
• 作为产物：
  描述：

  D-葡萄糖 、 1-O-isobutyryl-2-deoxy-β-glucopyranose 在 Lycopersicon pennellii 作用下， 以 various solvent(s) 为溶剂， 生成 1-O-isobutyryl-β-glucopyranose
  参考文献：
  名称：

  A survey of the nature of glucose acylation reactions in plant extracts

  摘要：

  A variety of plant species have been shown to catalyse anomeric acyl exchange from a number of 1-O-fatty-acyl-beta-glucoses as donor substrates to [(14)C]-glucose as an acceptor. The activity in wild tomato Lycopersicon penneliii has been analysed in detail by using analogs of glucose as accepters and a number of 1-O-acyl-beta-glucoses and 1-O-acyl-2-deoxyglucoses as acyl donors. Compared to 1-O-isobutyryl-beta-glucose, the analogous 1-O-isobutyryl-beta-2-deoxyglucose is an effective donor both to glucose (ca. 75%) and to 2-deoxyglucose (ca. 95%). On the contrary, compared to 1-O-isobutyryl-beta-glucose, 1-O-isobutyryl-alpha-2-deoxyglucose is a poor donor both to glucose (ca. 4%) and to deoxyglucose (ca. 6%). The glucose analogs free at the anomeric center such as 3-O-methylglucose and 2-deoxyglucose are competent acyl accepters from various 1-O-acyl-beta-glucoses whereas 1-O-methylglucose is not. The primary initial product of acyl transfer from 1-O-isobutyryl-beta-glucose to [(14)C]-glucose is beta-glucosidase-cleavable 1-O-acyl-[(14)C]-beta-glucose, whereas the isobutyryl-[(14)C]-3-O-methylglucose generated from 1-O-isobutyryl-beta-glucose and [(14)C]-3-O-methylglucose is beta-glucosidase-resistant. The transfer of the acyl group to 3-O-methylglucose occurs at the anomeric center; therefore the resistance to beta-glucosidase reflects the strict specificity of beta-glucosidase for glucose. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(99)00319-2

文献信息

• Chain length specific UDP-GLC: fatty acid glucosyltransferases
  申请人：Cornell Research Foundation, Inc.

  公开号：US06011145A1

  公开（公告）日：2000-01-04

  Enzyme activities which transfer glucose from uridine 5'-diphosphate glucose to fatty acids to form 1-O-acyl-.beta.-glucoses which act as acyl donors in the esterification of glucose and further esterification of partially acylated glucose and in the esterification of sucrose and further esterification of partially acylated sucrose, are separated according to specificity for transferring glucose to short, medium or long chain length fatty acids. DNA molecules coding for the enzyme activities are isolated. Methods for preparing 1-O-acyl-.beta.-D-glucoses comprise reacting uridine 5'-diphosphate glucose and fatty acid in the presence of the appropriate enzyme activity.

  酶活性可将葡萄糖从尿嘧啶5'-二磷酸葡萄糖转移至脂肪酸，形成1-O-酰基-β-葡萄糖，其在葡萄糖酯化和部分酰基化葡萄糖的进一步酯化以及蔗糖酯化和部分酰基化蔗糖的进一步酯化中作为酰基供体，根据对于将葡萄糖转移至短、中或长链长度脂肪酸的特异性进行分离。分离出编码该酶活性的DNA分子。制备1-O-酰基-β-D-葡萄糖的方法包括在适当的酶活性存在下，将尿嘧啶5'-二磷酸葡萄糖和脂肪酸反应。
• ACYLTRANSFERASE AND GENE ENCODING ACYLTRANSFERASE
  申请人：CORNELL RESEARCH FOUNDATION, INC.

  公开号：EP0909326A1

  公开（公告）日：1999-04-21
• US5756328A
  申请人：——

  公开号：US5756328A

  公开（公告）日：1998-05-26
• US6011145A
  申请人：——

  公开号：US6011145A

  公开（公告）日：2000-01-04
• US6066482A
  申请人：——

  公开号：US6066482A

  公开（公告）日：2000-05-23