benzyl 2-amino-2-deoxy-α-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2-amino-2-deoxy-α-D-glucopyranoside
• 英文别名: (2R,3S,4R,5R,6S)-5-amino-2-(hydroxymethyl)-6-phenylmethoxyoxane-3,4-diol
• 化学式: C₁₃H₁₉NO₅
• 分子量: 269.298
• InChiKey: ZLTAXQWRKKWROR-VEGXAWMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  105
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl 2-amino-2-deoxy-α-D-glucopyranoside 在 碳酸氢钠 作用下， 以 水 、 乙腈 为溶剂， 反应 24.0h， 生成 benzyl 4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloro-ethoxycarbonylamino)-α-D-glucopyranoside
  参考文献：
  名称：

  Enugala, Ramu; Marques, M. Manuel B., ARKIVOC, 2012, vol. 2012, # 6, p. 90 - 100

  摘要：

  DOI：
• 作为产物：
  描述：

  benzyl 2-deoxy-2-<(4,4-dimethyl-2,6-dioxocyclohexylidenemethyl)amino>-α-D-glucopyranoside 在 Amberlite-IRA-400 (OH-) 作用下， 以 水 、 丙酮 为溶剂， 反应 0.25h， 以100%的产率得到benzyl 2-amino-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  2-氨基-2-脱氧-d-葡萄糖的烷基葡糖吡喃糖苷和-呋喃糖苷的合成。2-脱氧-2-[（（4,4-二甲基-2,6-二氧代环己叉基甲基）氨基]-α-d-吡喃葡萄糖的晶体结构

  摘要：

  摘要在Et3N存在下，2-氨基-2-脱氧-d-葡萄糖酸盐与5,5-二甲基-2-苯基氨基亚甲基-1,3-环己二酮在MeOH中的反应得到2-脱氧-2-[（4， 4-二甲基-2，6-二氧代环己叉基甲基）氨基] -d-葡萄糖（6）的产率＞ 75％。在费歇尔条件下用不同的醇（MeOH，CH2 = CH = CH2OH，BnOH）对6进行糖基化，得到相应的烷基2-脱氧-2-[（4,4-二甲基-2,6-二氧代环己叉基甲基）-氨基]的混合物-α，β-d-吡喃葡萄糖苷和-α-d-葡糖呋喃糖苷。除去N-保护基团得到高产率的游离氨基脱氧糖吡喃糖苷和-呋喃糖苷。除了其他已知的糖苷之外，还获得了烯丙基和苄基2-氨基-2-脱氧-α-d-吡喃葡萄糖苷和乙基和烯丙基2-氨基-2-脱氧-α-β-葡糖呋喃糖苷。X射线晶体学研究表明6

  DOI：

  10.1016/0008-6215(87)80214-8

文献信息

• Protecting and linking groups for organic synthesis on solid supports
  申请人：Alchemia Pty Ltd

  公开号：US06765089B1

  公开（公告）日：2004-07-20

  This invention relates to methods for synthesis of organic compounds, and in particular to compounds useful as protecting and linking groups for use in the synthesis of peptides, oligosaccharides, glycopeptides and glycolipids. The invention provides protecting and linking groups that are useful in both solid phase and solution synthesis, and are particularly applicable to combinatorial synthesis.

  这项发明涉及有机化合物合成的方法，特别是用于合成肽、寡糖、糖肽和糖脂的保护和连接基团。该发明提供了在固相和溶液合成中均有用的保护和连接基团，特别适用于组合合成。
• Cleavage of unactivated amide bonds by ammonium salt-accelerated hydrazinolysis
  作者：Yuhei Shimizu、Megumi Noshita、Yuri Mukai、Hiroyuki Morimoto、Takashi Ohshima

  DOI：10.1039/c4cc02014f

  日期：——

  Hydrazinolysis of unactivated amide bonds is significantly accelerated by the addition of ammonium salts. The reactions proceed at 50-70 degrees C to give amines with broad substrate scope that outperforms existing amide bond cleavage reactions. Application to peptide and amino sugar derivatives is also demonstrated.

  铵盐的加入大大促进了未活化酰胺键的水合肼解反应。反应在50-70摄氏度下进行，得到的胺具有较宽的底物范围，胜过现有的酰胺键裂解反应。还证明了对肽和氨基糖衍生物的应用。
• Solid-phase oligosaccharide synthesis with tris(alkoxy)benzyl amine (BAL) safety-catch anchoring
  作者：Jakob F. Tolborg、Knud J. Jensen

  DOI：10.1039/a908446k

  日期：——

  A tris(alkoxy)benzylamine (BAL) handle strategy was developed for safety-catch anchoring of D-glucosamine derivatives in solid-phase synthesis of oligosaccharides; the linkage between the BAL handle and the amine proved stable to conc. TFA and Lewis acids, but after N-acylation the amide could be released by treatment with TFA–H2O (19∶1).

  开发了一种三（烷氧基）苄胺（BAL）处理策略，用于在寡糖的固相合成中安全地锚定 D-氨基葡萄糖衍生物；BAL 手柄和胺之间的连接被证明是稳定的。TFA 和路易斯酸，但在 N-酰化后，可以通过 TFA-H2O (19:1) 处理释放酰胺。
• Mycothiol disulfide reductase: solid phase synthesis and evaluation of alternative substrate analogues
  作者：Matthew J. G. Stewart、Vishnu Karthik Jothivasan、Andrew S. Rowan、Jennifer Wagg、Chris J. Hamilton

  DOI：10.1039/b716380k

  日期：——

  A solid phase synthesis of des-myo-inositol mycothiol disulfide and its alpha-configured methyl- and benzyl-glycoside derivatives has been developed. Kinetic characterisation of these compounds has demonstrated their viability as alternative substrates for use in mycothiol disulfide reductase enzyme assays.

  已经开发了脱肌醇肌醇硫醇二硫化物及其α-构型的甲基-和苄基-糖苷衍生物的固相合成。这些化合物的动力学表征已证明了它们作为可替代底物用于麦硫酚二硫键还原酶测定的可行性。
• Cross-functionalities of <i>Bacillus</i> deacetylases involved in bacillithiol biosynthesis and bacillithiol-S-conjugate detoxification pathways
  作者：Zhong Fang、Alexandra A. Roberts、Karissa Weidman、Sunil V. Sharma、Al Claiborne、Christopher J. Hamilton、Patricia C. Dos Santos

  DOI：10.1042/bj20130415

  日期：2013.9.1

  BshB, a key enzyme in bacillithiol biosynthesis, hydrolyses the acetyl group from N-acetylglucosamine malate to generate glucosamine malate. In Bacillus anthracis, BA1557 has been identified as the N-acetylglucosamine malate deacetylase (BshB); however, a high content of bacillithiol (~70%) was still observed in the B. anthracis ∆BA1557 strain. Genomic analysis led to the proposal that another deacetylase could exhibit cross-functionality in bacillithiol biosynthesis. In the present study, BA1557, its paralogue BA3888 and orthologous Bacillus cereus enzymes BC1534 and BC3461 have been characterized for their deacetylase activity towards N-acetylglucosamine malate, thus providing biochemical evidence for this proposal. In addition, the involvement of deacetylase enzymes is also expected in bacillithiol-detoxifying pathways through formation of S-mercapturic adducts. The kinetic analysis of bacillithiol-S-bimane conjugate favours the involvement of BA3888 as the B. anthracis bacillithiol-S-conjugate amidase (Bca). The high degree of specificity of this group of enzymes for its physiological substrate, along with their similar pH–activity profile and Zn2+-dependent catalytic acid–base reaction provides further evidence for their cross-functionalities.

  BshB 是杆菌硫醇生物合成过程中的一种关键酶，它水解 N-乙酰氨基葡萄糖苹果酸盐中的乙酰基，生成氨基葡萄糖苹果酸盐。在炭疽芽孢杆菌（Bacillus anthracis）中，BA1557 已被确定为 N-乙酰葡糖胺苹果酸盐脱乙酰酶（BshB）；然而，在炭疽芽孢杆菌 ∆BA1557 菌株中仍然观察到较高含量的杆菌硫醇（约 70%）。基因组分析结果表明，另一种脱乙酰酶可能在枯草硫酚的生物合成过程中表现出交叉功能。在本研究中，BA1557、其旁系亲属 BA3888 以及蜡样芽孢杆菌的直向同源酶 BC1534 和 BC3461 对 N-乙酰氨基葡萄糖苹果酸盐的脱乙酰酶活性进行了鉴定，从而为这一提议提供了生物化学证据。此外，预计脱乙酰酶还会通过形成 S-巯基加合物参与巴氏硫醇脱毒途径。杆菌硫醇-S-双烷共轭物的动力学分析表明，BA3888 是炭疽杆菌的杆菌硫醇-S-共轭物氨化酶（Bca）。这组酶对其生理底物的高度特异性，以及它们相似的 pH 活性曲线和 Zn2+ 依赖性催化酸碱反应，进一步证明了它们的跨功能性。