phenyl 2-acetamido-2-deoxy-1-thio-α-D-glucopyranoside | 1228577-52-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2-acetamido-2-deoxy-1-thio-α-D-glucopyranoside
• 英文别名: phenyl-2-acetamido-2-deoxy-1-thio-α-D-glucopyranoside；N-((2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-2-(phenylthio)tetrahydro-2H-pyran-3-yl)acetamide；N-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-phenylsulfanyloxan-3-yl]acetamide
• CAS: 1228577-52-3
• 化学式: C₁₄H₁₉NO₅S
• 分子量: 313.375
• InChiKey: FRBANKZKTRTKBB-DHGKCCLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  124
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  phenyl-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-α-D-glucopyranoside 在 甲醇 、 sodium methylate 作用下， 以98%的产率得到phenyl 2-acetamido-2-deoxy-1-thio-α-D-glucopyranoside
  参考文献：
  名称：

  Conjugates of plumbagin and phenyl-2-amino-1-thioglucoside inhibit MshB, a deacetylase involved in the biosynthesis of mycothiol

  摘要：

  N-Acetylglucosaminylinositol (GlcNAc-Ins)-deacetylase (MshB) and mycothiol-S-conjugate amidase (Mca), structurally related amidases present in mycobacteria and other Actinomycetes, are involved in the biosynthesis of mycothiol and in the detoxification of xenobiotics as their mycothiol-S-conjugates, respectively. With substrate analogs of GlcNAc-Ins, MshB showed a marked preference for inositol as the aglycon present in GlcNAc-Ins. The inhibition of MshB and Mca by 10 thioglycosides, 7 cyclohexyl-2-deoxy-2-C-alkylglucosides, and 4 redox cyclers was evaluated. The latter contained plumbagin tethered via 2 to 5 methylene carbons and an amide linkage to phenyl-2-deoxy-2-amino-1-thio-alpha-D-glucopyranoside. These proved to be the most potent amongst the 21 compounds tested as inhibitors of MshB. Their inhibitory potency varied with the length of the spacer, with the compound with longest spacer being the most effective. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.02.049

文献信息

• The α-Thioglycoligase Derived from a GH89 α-<i>N</i>-Acetylglucosaminidase Synthesises α-<i>N</i>-Acetylglucosamine-Based Glycosides of Biomedical Interest
  作者：Ndivhuwo Olga Tshililo、Andrea Strazzulli、Beatrice Cobucci-Ponzano、Luisa Maurelli、Roberta Iacono、Emiliano Bedini、Maria Michela Corsaro、Erick Strauss、Marco Moracci

  DOI：10.1002/adsc.201601091

  日期：2017.2.20

  acceptors. The synthetic potential of the Glu483 alanine mutant as an α‐thioglycoligase – only the third biocatalyst with this stereospecificity reported to date, and the first selective for the N‐acetylglucosamine moiety – was demonstrated by producing for the first time N‐acetyl‐α‐d‐glucosaminyl azide and N‐acetylglucosamine α‐thioglycosides in high yields. To showcase the application of such compounds

  我们在这里报告了一种新型α-硫代糖苷酶的制备方法，该酶可用于快速高效合成基于α - N-乙酰氨基葡萄糖的糖苷。以GH89家族产气荚膜梭菌的α - N-乙酰氨基葡糖苷酶（根据碳水化合物活性酶分类）为起点，我们制备了谷氨酸/酸残基483中的突变体，发现它们具有不同的合成效率（最大）。在活化的供体和合适的受体存在下，在24小时后的收率> 80％。Glu483丙氨酸突变体作为α-硫代糖苷酸酶的合成潜力–迄今为止，仅报道了具有这种立体特异性的第三种生物催化剂，并且对N具有选择性乙酰氨基葡萄糖基部分-被产生用于首次展示ñ -乙酰基α- d -glucosaminyl叠氮化物和Ñ以高收率乙酰氨基葡萄糖α-硫代糖苷。为了展示此类化合物的应用，我们证明了它们提供了野生型CpGH89保护，使其免受热解折叠，证明了它们作为药理分子伴侣治疗粘多糖贮积症IIIB（Sanfilippo综合征）的潜力。
• Conjugates of plumbagin and phenyl-2-amino-1-thioglucoside inhibit MshB, a deacetylase involved in the biosynthesis of mycothiol
  作者：David W. Gammon、Daniel J. Steenkamp、Vuyo Mavumengwana、Mohlopheni J. Marakalala、Theophilus T. Mudzunga、Roger Hunter、Muganza Munyololo

  DOI：10.1016/j.bmc.2010.02.049

  日期：2010.4

  N-Acetylglucosaminylinositol (GlcNAc-Ins)-deacetylase (MshB) and mycothiol-S-conjugate amidase (Mca), structurally related amidases present in mycobacteria and other Actinomycetes, are involved in the biosynthesis of mycothiol and in the detoxification of xenobiotics as their mycothiol-S-conjugates, respectively. With substrate analogs of GlcNAc-Ins, MshB showed a marked preference for inositol as the aglycon present in GlcNAc-Ins. The inhibition of MshB and Mca by 10 thioglycosides, 7 cyclohexyl-2-deoxy-2-C-alkylglucosides, and 4 redox cyclers was evaluated. The latter contained plumbagin tethered via 2 to 5 methylene carbons and an amide linkage to phenyl-2-deoxy-2-amino-1-thio-alpha-D-glucopyranoside. These proved to be the most potent amongst the 21 compounds tested as inhibitors of MshB. Their inhibitory potency varied with the length of the spacer, with the compound with longest spacer being the most effective. (C) 2010 Elsevier Ltd. All rights reserved.