laminaratrehalose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: laminaratrehalose
• 英文别名: Glc(b1-3)Glc(a1-1a)Glc；(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5R,6R)-3,5-dihydroxy-2-(hydroxymethyl)-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₁₈H₃₂O₁₆
• 分子量: 504.442
• InChiKey: VBMQKUDEYKVQNV-LMSCTTHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.8
• 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：
  269
• 氢给体数：
  11
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  lipid Q 在 氢氧化钾 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 30.0h， 生成 laminaratrehalose
  参考文献：
  名称：

  A novel trisaccharide glycolipid biosurfactant containing trehalose bears ester-linked hexanoate, succinate, and acyloxyacyl moieties: NMR and MS characterization of the underivatized structure

  摘要：

  A Gram-positive actinomycete growing on n-hexadecane secreted a family of anionic glycolipid surfactant homologs,The major homolog, with a molecular weight of 1210.6347, had the formula C58H98O26. Following mild alkaline saponification,H-1 and C-13 NMR spectroscopy were used to characterize the non-reducing trisaccharide backbone: beta-Glcp-(1 --> 3)-alpha-Glcp-(1 <-> 1)-alpha-Glcp ('laminaratrehalose'). Hexanoate, succinate, 3-hydroxyoctanoate, and 3-hydroxydecanoate were found in 3:1:1:1 molar ratio using GC-EIMS analysis of fatty acid methyl esters (FAME) prepared by transesterification. Mie found that the beta-hydroxy acids bore secondary hexanoate chains in 3-O-ester linkage, giving acyloxyacyl anions of appropriate mi; in FABMS and FABMS/MS spectra. COSY, HETCOR, HMBC, and HMQC NMR experiments established the acylation pattern: succinate at C-2 of the terminal alpha-glucopyranose ring; hexanoate at C-3 " of the beta-glucopyranose ring; 3-hexanoyloxydecanoate and 3-hexanoyloxydecanoate at the 2'- and 4-positions. In FABMS spectra, the homologs flanked the molecular ion by +/- 14 and +/- 28 amu, suggesting heterogeneity in acyl chain length. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00122-6

文献信息

• First Direct Glycosylation of Unprotected Nonreducing Mono- and Disaccharides
  作者：Andreas Steinmann、Julian Thimm、Joachim Thiem

  DOI：10.1002/ejoc.200700504

  日期：2007.11

  glycosyl acceptors is reported by random glycosylation leading to all possible regioisomers. For such systems conventional glycosylation methods such as Koenigs–Knorr glycosylation, Schmidt's trichloroacetimidate glycosylation and reactions employing glycosyl fluoride donors fail entirely. Starting from unprotected nonreducing saccharides, the glycosylation of β-glucosylated and β-galactosylated monosaccharides

  完全无保护的糖基受体的第一个单步随机糖基化方法报告通过随机糖基化导致所有可能的区域异构体。对于此类系统，传统的糖基化方法，例如 Koenigs-Knorr 糖基化、Schmidt 的三氯乙酰亚胺糖基化和使用糖基氟供体的反应完全失败。从未受保护的非还原糖开始，研究了 β-葡萄糖基化和 β-半乳糖基化单糖（Glc、Gal）、对称二糖（例如 α,α-海藻糖）以及不对称二糖（例如蔗糖）的糖基化。检查了碱类型和浓度的影响。生成了几个二糖和三糖文库。所有区域异构体以大致相等的比例形成，用快速柱色谱法实现部分分离。尽管与经典的保护基化学相比，总体产率似乎较低，但这种合成努力可能更胜一筹，尤其是在获得更高的糖类方面。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• A novel trisaccharide glycolipid biosurfactant containing trehalose bears ester-linked hexanoate, succinate, and acyloxyacyl moieties: NMR and MS characterization of the underivatized structure
  作者：Steven Wynn Esch、Martha D. Morton、Todd D. Williams、Clarence S. Buller

  DOI：10.1016/s0008-6215(99)00122-6

  日期：1999.6

  A Gram-positive actinomycete growing on n-hexadecane secreted a family of anionic glycolipid surfactant homologs,The major homolog, with a molecular weight of 1210.6347, had the formula C58H98O26. Following mild alkaline saponification,H-1 and C-13 NMR spectroscopy were used to characterize the non-reducing trisaccharide backbone: beta-Glcp-(1 --> 3)-alpha-Glcp-(1 <-> 1)-alpha-Glcp ('laminaratrehalose'). Hexanoate, succinate, 3-hydroxyoctanoate, and 3-hydroxydecanoate were found in 3:1:1:1 molar ratio using GC-EIMS analysis of fatty acid methyl esters (FAME) prepared by transesterification. Mie found that the beta-hydroxy acids bore secondary hexanoate chains in 3-O-ester linkage, giving acyloxyacyl anions of appropriate mi; in FABMS and FABMS/MS spectra. COSY, HETCOR, HMBC, and HMQC NMR experiments established the acylation pattern: succinate at C-2 of the terminal alpha-glucopyranose ring; hexanoate at C-3 " of the beta-glucopyranose ring; 3-hexanoyloxydecanoate and 3-hexanoyloxydecanoate at the 2'- and 4-positions. In FABMS spectra, the homologs flanked the molecular ion by +/- 14 and +/- 28 amu, suggesting heterogeneity in acyl chain length. (C) 1999 Elsevier Science Ltd. All rights reserved.