triethylammonium dibenzyl phosphate | 119095-47-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: triethylammonium dibenzyl phosphate
• 英文别名: dibenzyl phosphate；Triaethylamin-dibenzylphosphat；Triethyl-ammonium dibenzyl phosphate；dibenzyl phosphate;triethylazanium
• CAS: 119095-47-5
• 化学式: C₆H₁₅N*C₁₄H₁₅O₄P
• 分子量: 379.436
• InChiKey: TXZVKSNFCZUARP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  63
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  triethylammonium dibenzyl phosphate 、 methyl tri-O-benzoyl-α-D-arabinofuranoside 在 二氯甲烷 、 氢溴酸 、 溶剂黄146 作用下， 生成 O¹-Phosphono-α-D-arabinofuranose
  参考文献：
  名称：

  Phosphorylated Sugars. V.¹ Syntheses of Arabinofuranose and Arabinopyranose 1-Phosphates

  摘要：

  DOI：

  10.1021/ja01541a055

文献信息

• Large-scale synthesis of β-l-fucopyranosyl phosphate and the preparation of GDP-β-l-fucose
  作者：Kim Adelhorst、George M. Whitesides

  DOI：10.1016/0008-6215(93)80022-7

  日期：1993.4

  Abstract A practical 15-mmol large-scale synthesis of β- l -fucopyranosyl dicyclohexylammonium phosphate from l -fucose in 63% overall yield was developed. The synthesis took advantage of a neighboring Bz-2 group participating in a Koenigs-Knorr-like glycosylation. The sugar phosphate was transformed into the activated sugar nucleoside, guanosine diphosphate β- l -fucopyranose, on a gram scale.

  摘要开发了一种实用的由L-岩藻糖以15％的大规模收率合成15-mmol-β-岩藻糖基二环己基磷酸铵的化合物。该合成利用了参与Koenigs-Knorr样糖基化的相邻Bz-2基团的优势。以克为单位，将糖磷酸酯转化成活化的糖核苷，鸟苷二磷酸β-1-呋喃葡萄糖。
• Mechanistic Investigation of UDP-Galactopyranose Mutase from <i>Escherichia </i><i>c</i><i>oli</i> Using 2- and 3-Fluorinated UDP-Galactofuranose as Probes
  作者：Qibo Zhang、Hung-wen Liu

  DOI：10.1021/ja010473l

  日期：2001.7.1

  The galactofuranose moiety found in many surface constituents of microorganisms is derived from UDP-D-galactopyranose (UDP-Galp) via a unique ring contraction reaction catalyzed by UDP-Galp mutase. This enzyme, which has been isolated from several bacterial sources, is a flavoprotein. To study this catalysis, the cloned Escherichia coli mutase was purified and two fluorinated analogues, UDP-[2-F]Galf(9) and UDP-[3-F]Galf(10), were chemically synthesized. These two compounds were found to be substrates for the reduced UDP-Galp mutase with the K-m values determined to be 65 and 861 muM for 9 and 10, respectively, and the corresponding k(cat) values estimated to be 0.033 and 5.7 s(-1). Since the fluorine substituent is redox inert, a mechanism initiated by the oxidation of 2-OH or 3-OH on the galactose moiety can thus be firmly ruled out. Furthermore, both 9 and 10 are poorer substrates than UDP-Galf, and the rate reduction for 9 is especially significant. This finding may be ascribed to the inductive effect of the 2-F substituent that is immediately adjacent to the anomeric center, and is consistent with a mechanism involving formation of oxocarbenium intermediates or transition states during turnover. Interestingly, under nonreducing conditions, compounds 9 and 10 are not substrates, but instead are inhibitors for the mutase. The inactivation by 10 is time-dependent, active-site-directed. and irreversible with a K-I of 270 muM and a k(inact) of 0.19 min(-1). Since the K-I value is similar to K-m, the observed inactivation is unlikely a result of tight binding. To our surprise, the inactivated enzyme could be regenerated in the presence of dithionite, and the reduced enzyme is resistant to inactivation by these fluorinated analogues. It is possible that reduction of the enzyme-bound FAD may induce a conformational change that facilitates the breakdown of the putative covalent enzyme-inhibitor adduct to reactivate the enzyme. It is also conceivable that the reduced flavin bears a higher electron density at N-1, which may play a role in preventing the formation of the covalent adduct or facilitating its breakdown by charge stabilization of the oxocarbenium intermediates/transition states. Clearly, this study has led to the identification of a potent inactivator (10) for this enzyme, and study of its inactivation has also shed light on the possible mechanism of this mutase.
• Phosphorylated Sugars. II. The Preparation of the Anomeric Methyl 5-O-Benzyl-D-ribofuranoside 2,3-Cyclic Carbonates and the Study of their Reactions with Hydrogen Bromide in Acetic Acid
  作者：G. M. Tener、H. G. Khorana

  DOI：10.1021/ja01559a055

  日期：1957.1
• Chemoenzymatic synthesis of GM3, Lewis x and sialyl Lewis x oligosaccharides in 13C-enriched form
  作者：Mark A. Probert、Mark.J. Milton、Richard Harris、Sergio Schenkman、Jonathan M. Brown、Steven W. Homans、Robert A. Field

  DOI：10.1016/s0040-4039(97)01304-x

  日期：1997.8

  In connection with studies on the solution and protein-bound conformation of oligosaccharides, we had reason to consider the application of C-13-enriched sugars. Herein we describe the synthesis of ganglioside GM(3) trisaccharide (1), Lewis x trisaccharide (2) and the sialyl Lewis x tetrasaccharide (3) from [U-C-13]-D-Glc, [U-C-13]-L-Gal and [U-C-13]-pyruvate. (C) 1997 Elsevier Science Ltd.
• Synthesis of 2-deoxy-2-fluoro analogs of polyprenyl β-d-arabinofuranosyl phosphates
  作者：Maju Joe、Todd L. Lowary

  DOI：10.1016/j.carres.2006.08.020

  日期：2006.11

  Described is the synthesis of polyprenyl 2-deoxy-2-fluoro-beta-D-arabinofuranosyl phosphate derivatives, including an analog of decaprenyl P-D-arabinofuranosyl phosphate, the donor species used by the arabinosyltransferases involved in mycobacterial cell-wall biosynthesis. The targets were synthesized via a route involving the synthesis of a protected beta-D-arabinofuranosyl phosphate derivative, its coupling with a polyprenyl trichloroacetimidate, and then deprotection of the resulting product. The use of arabinofuranosyl phosphates with the monosaccharide hydroxyl groups protected as either silyl ethers or benzoate esters was explored. Although the coupling yields between the phosphate and polyprenyl trichloroacetimidates were comparable with either type of protecting group, access to the benzoyl-protected derivative was more efficient and therefore gave the products in higher overall yield. (c) 2006 Elsevier Ltd. All rights reserved.