2-萘基 2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧吡喃己糖苷 | 131531-80-1

• 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-3,4,6-三-O-乙酰基-2-脱氧吡喃己糖苷
• 中文别名: 2-萘基2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧吡喃己糖苷
• 英文名称: 2-napthyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside
• 英文别名: 1-(2-naphthyl) 3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranoside；[2]naphthyl-(tri-O-acetyl-2-acetylamino-2-deoxy-β-D-glucopyranoside)；[2]Naphthyl-(tri-O-acetyl-2-acetylamino-2-desoxy-β-D-glucopyranosid)；2-Naphthyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-glucopyranoside；[(2R,3S,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-naphthalen-2-yloxyoxan-2-yl]methyl acetate
• CAS: 131531-80-1
• 化学式: C₂₄H₂₇NO₉
• 分子量: 473.48
• InChiKey: CHHFGHQMWZQINE-MRKXFKPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-萘基 2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧吡喃己糖苷 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以89%的产率得到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
• 作为产物：
  描述：

  2-萘酚 、 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 、 四丁基溴化铵 作用下， 以 二氯甲烷 为溶剂， 反应 0.83h， 以65%的产率得到2-萘基 2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧吡喃己糖苷
  参考文献：
  名称：

  Design of N-acetyl-6-sulfo-β-d-glucosaminide-based inhibitors of influenza virus sialidase

  摘要：

  Biological activity of N-acetyl-6-SUIfO-beta-D-glucosaminides (6-sulfo-GlcNAc 1) having a structural homology to N-acetylneuraminic acid (Neu5Ac 2) and 2-deoxy-2,3-dehydro-N-acetylneuraminic acid (Neu5Ac2en 3) was examined in terms of inhibitory activity against influenza virus sialidase (influenza, A/Memphis/l/71 H3N2). pNP 6-Sulfo-GlcNAc la was proved to show substantial activity to inhibit the virus sialidaSe IC50 2.8 mM), though p-nitrophenyl (pNP) GlcNAc without 6-sulfo group and pNP 6-sulfo-GlcNH(3)(+) 1b without 2-NHAc showed little activity IC50 > 50 mM). The activity was enhanced nearly 100-fold when the pNP group of la was converted to p-acetamidophenyl one 5 (IC50 = 30 muM) or replaced with 1-naphthyl 6 IC50 = 10 muM) or n-propyl one 8 (IC50 = 11 muM) (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.01.013

文献信息

• Roy, Rene; Tropper, Francois, Synthetic Communications, 1990, vol. 20, # 14, p. 2097 - 2102
  作者：Roy, Rene、Tropper, Francois

  DOI：——

  日期：——
• ——
  作者：V. O. Kur'yanov、T. A. Chupakhina、A. E. Zemlyakov、S. A. Kotlyar、G. L. Kamalov、V. Ya. Chirva

  DOI：10.1023/a:1012988719296

  日期：——

  Glycosylation of various phenols with alpha -D-glucosaminyl chloride peracetate in a solid phase-liquid system catalyzed by crown compounds was studied. The highest yields of aryl beta -glycosides were observed at room temperature in acetonitrile using anhydrous potassium carbonate as a base. The optimum phenol-glycosyl donor-base-crown ether ratio was 1 : 1 : 1 : 0.2.
• 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：——