4-甲基伞形酮基 beta-D-N,N’-二乙酰基壳二糖糖苷 | 53643-12-2

• 物质功能分类: 生物化工 - 糖类化合物 - 双糖
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: 4-甲基伞形酮基 beta-D-N,N’-二乙酰基壳二糖糖苷
• 中文别名: 4-甲基伞形酮基beta-D-N,N’-二乙酰基壳二糖糖苷；4-甲基umbelliferylN,N-二乙酰基-β-d-chitobioside；4-甲基伞形酮基BETA-D-N,N'-二乙酰基壳二糖糖苷；4-甲基伞形酮基 BETA-D-N,N"-二乙酰基壳二糖糖苷；4-甲基伞形酮基 BETA-D-N,N'-二乙酰基壳二糖糖苷
• 英文名称: 4-methylumbelliferyl N,N'-diacetyl-β-D-chitobioside
• 英文别名: 4-methylumbelliferyl β-D-N, N′ -diacetylchitobioside hydrate；4-Methyl-umbelliferyl-N-acetyl-chitobiose；N-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4R,5R,6S)-5-acetamido-4-hydroxy-2-(hydroxymethyl)-6-(4-methyl-2-oxochromen-7-yl)oxyoxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 53643-12-2
• 化学式: C₂₆H₃₄N₂O₁₃
• 分子量: 582.562
• InChiKey: UPSFMJHZUCSEHU-JYGUBCOQSA-N

物化性质

• 熔点：
  >187°C (dec.)
• 溶解度：
  DMF：10 mg/mL，澄清，无色

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  41
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  223
• 氢给体数：
  7
• 氢受体数：
  13

安全信息

• WGK Germany：
  3
• 海关编码：
  29322090
• 储存条件：
  -20°C

反应信息

• 作为反应物：
  描述：

  4-甲基伞形酮基 beta-D-N,N’-二乙酰基壳二糖糖苷 在 苯磺酰胺 citrate-phosphate buffer 、 chitinase B from Serratia marsensens 、 psammaplin A 作用下， 反应 0.17h， 生成 羟甲香豆素
  参考文献：
  名称：

  Psammaplin A, a chitinase inhibitor isolated from the fijian marine sponge Aplysinella rhax

  摘要：

  Several brominated tyrosine derived compounds. psammaplins A (1), K (2) and L (3) as well as bisaprasin (4) were isolated from the Fijian marine sponge Aplysinella rhax during a bioassay guided isolation protocol. Their structures were determined using NMR and MS techniques. Psammaplin A was found to moderately inhibit chitinase B from Serratia marcescens, the mode of inhibition being non-competitive, Crystallographic studies suggest that a disordered psammaplin A molecule is bound near the active site. Interestingly, psammaplin A was found to be a potent antifungal agent. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00372-8

文献信息

• An efficient synthesis of argifin: A natural product chitinase inhibitor with chemotherapeutic potential
  作者：Mark J. Dixon、Ole A. Andersen、Daan M.F. van Aalten、Ian M. Eggleston

  DOI：10.1016/j.bmcl.2005.07.068

  日期：2005.11

  The first synthesis of the cyclopentapeptide family 18 chitinase inhibitor argifin has been achieved by a combination of solid phase and solution chemistry. Synthetic argifin is a nanomolar inhibitor of chitinase B1 from Aspergillus fumigatus and the high-resolution X-ray structure of the synthesized material in complex with the same enzyme is identical to that previously obtained for the natural product

  环五肽家族18几丁质酶抑制剂argifin的首次合成是通过固相和溶液化学的结合来实现的。合成的argifin是烟曲霉的几丁质酶B1的纳摩尔抑制剂，与相同酶复合的合成材料的高分辨率X射线结构与以前从天然产物中获得的相同。
• Chemoenzymatic synthesis of N-linked neoglycoproteins through a chitinase-catalyzed transglycosylation
  作者：Cishan Li、Wei Huang、Lai-Xi Wang

  DOI：10.1016/j.bmc.2008.08.042

  日期：2008.9

  A novel application of the Bacillus sp. chitinase for the chemoenzymatic synthesis of N-linked neoglycoproteins is described. Three chitinases with different molecular size were purified from the crude chitinase preparation. The purified chitinases were evaluated for their hydrolytic and transglycosylation activity. One chitinase with a molecular size of 100 kDa (Chi100) was identified to be the one with highest transglycosylation/ hydrolysis ratio. Chi100 could effectively recognize LacNAc-oxazoline and Man alpha 1,3Glc beta 1,4GlcNAc-oxazoline as the donor substrate to glycosylate Asn-linked GlcNAc, while it was unable to recognize Man beta 1,4GlcNAc and Man(3)GlcNAc-oxazolines as the donor substrates. The chitinase-catalyzed transglycosylation was successfully extended to the remodeling of ribonuclease B to afford neoglycoproteins. Although the yield needs to be optimized, the chitinase-catalyzed transglycosylation provides a potentially useful tool for the synthesis of neoglycoproteins carrying novel N-linked oligosaccharides. (C) 2008 Elsevier Ltd. All rights reserved.
• Chemo- and enzymatic synthesis of partially and fully N -deacetylated 4-methylumbelliferyl chitobiosides: Fluorogenic substrates for chitinase
  作者：Yuji Honda、Shinji Tanimori、Mitsunori Kirihata、Satoshi Kaneko、Ken Tokuyasu、Masayuki Hashimoto、Takeshi Watanabe

  DOI：10.1016/s0960-894x(00)00116-5

  日期：2000.4

  Partially and fully N-deacetylated 4-methylumberlliferyl chitobioside (1) derivatives, such as GlcN-GlcNAc-UMB (2), GlcNAc-GlcN-UMB (3), and (GlcN)(2)-UMB (4), were synthesized using chemo- and enzymatic procedure. Fluorescent aglycon was released from the chitobiosides 1, 2 and 3 by the action of chitinase. These UMB glycosides of hererochitobiose were versatile probes for the investigation of substrate binding chitinase from various sources. (C) 2000 Elsevier Science Ltd. All rights reserved.