2-萘基 2-乙酰氨基-2-脱氧-beta-D-吡喃葡萄糖苷 | 131531-82-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-萘基 2-乙酰氨基-2-脱氧-beta-D-吡喃葡萄糖苷
• 中文别名: 2-萘基2-乙酰氨基-2-脱氧-beta-D-吡喃葡萄糖苷
• 英文名称: 1-(2-naphthyl) 2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: 2-naphthyl 2-acetamido-2-deoxy-β-D-glucopyranoside；[2]naphthyl-(2-acetylamino-2-deoxy-β-D-glucopyranoside)；[2]Naphthyl-(2-acetylamino-2-desoxy-β-D-glucopyranosid)；2-Naphthyl 2-acetamido-2-deoxy-b-D-glucopyranoside；N-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-naphthalen-2-yloxyoxan-3-yl]acetamide
• CAS: 131531-82-3
• 化学式: C₁₈H₂₁NO₆
• 分子量: 347.368
• InChiKey: QKMSGRRTZKSWCS-DUQPFJRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  108
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-萘基 2-乙酰氨基-2-脱氧-beta-D-吡喃葡萄糖苷 在 N-羟基丁二酰亚胺 、 sodium hydride 、 对甲苯磺酸 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 10.0h， 生成 O-(2-naphthyl 2-acetamido-2-deoxy-β-D-glucopyranosid-3-yl)-D-lactoyl-L-alanyl-D-isoglutamine benzyl ester
  参考文献：
  名称：

  摘要：

  Synthesis of N-acetylmuramyl-L-alanyl-D-isoglutamine phenyl and (2-naphthyl) beta -glycosides, novel muramyl dipeptide derivatives with phenolic aglycons, was reported. The starting N-acetylglucosamine aryl glycosides were obtained by glycosylation of phenols with peracetylated alpha -glucosaminyl chloride under the conditions of phase-transfer catalysis and used for the synthesis of 4,6-O-isopropylidene-N-acetylmyramic acid aryl beta -glycosides. Condensation of these derivatives with a dipeptide and subsequent deprotection resulted in the intended glycopeptides.

  DOI：

  10.1023/a:1012940803366
• 作为产物：
  描述：

  2-乙酰氨基-3,4,6-三-O-乙酰-2-脱氧-α-D-吡喃葡萄糖酰基氯 在 sodium hydroxide 、 苄基三乙基氯化铵 、 sodium methylate 作用下， 以 甲醇 、 氯仿 为溶剂， 生成 2-萘基 2-乙酰氨基-2-脱氧-beta-D-吡喃葡萄糖苷
  参考文献：
  名称：

  摘要：

  Synthesis of N-acetylmuramyl-L-alanyl-D-isoglutamine phenyl and (2-naphthyl) beta -glycosides, novel muramyl dipeptide derivatives with phenolic aglycons, was reported. The starting N-acetylglucosamine aryl glycosides were obtained by glycosylation of phenols with peracetylated alpha -glucosaminyl chloride under the conditions of phase-transfer catalysis and used for the synthesis of 4,6-O-isopropylidene-N-acetylmyramic acid aryl beta -glycosides. Condensation of these derivatives with a dipeptide and subsequent deprotection resulted in the intended glycopeptides.

  DOI：

  10.1023/a:1012940803366

文献信息

• An acceptor analogue of β-1,4-galactosyltransferase: Substrate, inhibitor, or both?
  作者：Jingqian Jiang、Gerd K. Wagner

  DOI：10.1016/j.carres.2017.08.012

  日期：2017.10

  Many glycosyltransferase inhibitors in the literature are structurally derived from the donor or acceptor substrate of the respective enzyme. A representative example is 2-naphthyl b-D-GlcNAc, a synthetic GlcNAc glycoside that has been reported as a galactosyltransferase inhibitor. This GlcNAc derivative is attractive as a chemical tool compound for biological and biochemical studies because of its reported potency as an inhibitor, and its short and straightforward synthesis from readily available starting materials. We report that in our hands, 2-naphthyl b-D-GlcNAc behaved, unexpectedly, as an acceptor substrate of the inverting b-1,4-galactosyltransferase (b-1,4-GalT) from bovine milk. This substrate activity has not previously been described. We found that 2-naphthyl b-D-GlcNAc can be an acceptor substrate both for recombinantly expressed b-1,4-GalT, and for a commercial batch of the same enzyme, and both in the presence and absence of bovine serum albumin (BSA). As expected for a full acceptor substrate, this substrate activity was time-and concentration-dependent. Additional experiments show that the observed inhibitor/substrate switch is facilitated by a phosphatase that is an essential component of our enzyme-coupled glycosyltransferase assay. These findings suggest that the behaviour of 2naphthyl b-D-GlcNAc and related acceptor-based glycosyltransferase inhibitors is strongly dependent on the individual assay conditions. Our results therefore have important implications for the use of 2naphthyl b-D-GlcNAc and related glycosides as tool compounds in glycobiology and glycobiochemistry. (C)2017 The Authors. Published by Elsevier Ltd.
• Acceptor substrate-based selective inhibition of galactosyltransferases
  作者：Sang J Chung、Shuichi Takayama、Chi-Huey Wong

  DOI：10.1016/s0960-894x(98)00618-0

  日期：1998.12

  This paper describes the discovery of glycosyl acceptor analogs as potent and selective inhibitors of alpha-1,3- and beta-1,4-galactosyltransferases. Incorporation of an appropriate aromatic group to the aglycon position of the enzyme's accepters results in a strong inhibition, representing the first and most potent small uncharged molecules as selective inhibitors of these two enzymes and thus providing a new strategy for the development of selective glycosyltransferase inhibitors. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
• Fujise; Yokoyama, Nippon Kagaku Zasshi, 1951, vol. 72, p. 728
  作者：Fujise、Yokoyama

  DOI：——

  日期：——
• ROY, RENE;TROPPER, FRANCOIS, SYNTH. COMMUN., 20,(1990) N4, C. 2097-2102
  作者：ROY, RENE、TROPPER, FRANCOIS

  DOI：——

  日期：——
• PROCEDE D'IDENTIFICATION DE CANDIDA ALBICANS AU MOYEN DE SUBSTRATS CHROMOGENES
  申请人：DIAGNOSTICA STAGO (société anonyme)

  公开号：EP0476107B1

  公开（公告）日：1996-06-19