4-硝基苯基-β-木三糖苷 | 173468-29-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-硝基苯基-β-木三糖苷
• 英文名称: p-nitrophenyl β-D-xylopyranosyl-(1->4)-β-D-xylopyranosyl-(1->4)-β-D-xylopyranoside
• 英文别名: 4-nitrophenyl O-β-D-xylopyranosyl-(1<*>4)-O-β-D-xylopyranosyl-(1<*>4)-β-D-xylopyranoside；4-Nitrophenyl b-D-xylotrioside；(2S,3R,4S,5R)-2-[(3R,4R,5R,6S)-6-[(3R,4R,5R,6S)-4,5-dihydroxy-6-(4-nitrophenoxy)oxan-3-yl]oxy-4,5-dihydroxyoxan-3-yl]oxyoxane-3,4,5-triol
• CAS: 173468-29-6
• 化学式: C₂₁H₂₉NO₁₅
• 分子量: 535.459
• InChiKey: HJRGODZIIOLZRT-MVOFOWCMSA-N

物化性质

• 沸点：
  849.0±65.0 °C(Predicted)
• 密度：
  1.70±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  243
• 氢给体数：
  7
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  4-硝基苯基-β-木三糖苷 在 cellodextrin phosphorylase 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4,6-O-benzylidene-4-nitrophenyl-β-4³-glucosyl-β-xylotrioside
  参考文献：
  名称：

  新型底物，用于自动和手动测定1,4-β-木聚糖内切酶。

  摘要：

  1，4-β-木聚糖内切酶（EC 3.2.1.8）被广泛应用于动物饲料，酿造，烘焙，生物燃料，洗涤剂和纸浆（纸）等行业。尽管其重要性，迄今为止尚未描述基于使用化学确定的底物对该酶进行快速，可靠，可再现，可自动化的测定。本文报道了一种新的酶偶联测定方法，称为XylX6测定法，其采用了新型底物，即4，6-O-（3-酮丁烯）-4-硝基苯基-β-45-O-葡糖基-木糖基opentaoside。本文讨论了底物和相关测定法的发展，并彻底研究了XylX6测定法与传统还原糖测定法获得的活性值之间的关系及其特异性和可重复性。

  DOI：

  10.1016/j.carres.2017.02.009
• 作为产物：
  描述：

  4-硝基苯基-BETA-D-吡喃木糖苷 在 吡啶 、 甲醇 、 N-碘代丁二酰亚胺 、 4 A molecular sieve 、 sodium methylate 、 silver trifluoromethanesulfonate 、 二正丁基氧化锡 、 硫脲 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 14.67h， 生成 4-硝基苯基-β-木三糖苷
  参考文献：
  名称：

  dp 2–4的β-（1→4）-d-木糖寡糖的2-和4-硝基苯基β-糖苷的合成

  摘要：

  通过二丁基氧化锡介导的酰化作用，将2-和4-硝基苯基β-d-吡喃吡喃糖苷（4和5）转化为相应的2,3-二-O-苯甲酰基衍生物11和15。炭柱色谱法，由市售材料制成，并转化为二糖和三糖甲基1-硫代-β-糖苷36和37。β-（1→4）-d-的2-和4-硝基苯基β-糖苷dp 2–4的木糖寡糖是通过N-碘代琥珀酰亚胺-三氟甲磺酸银促进的缩合反应合成的，使用11和15作为糖基受体，乙基1-硫代-β-d-吡喃吡喃糖苷三乙酸酯16、36和37作为糖基供体。 。还描述了改进的4和5的制备方法以及1-萘β-d-吡喃吡喃糖苷的合成，以及2-和4-硝基苯基β-吡喃二糖苷的替代方法。

  DOI：

  10.1016/0008-6215(95)00214-e

文献信息

• A New Archaeal β-Glycosidase from Sulfolobus solfataricus
  作者：Beatrice Cobucci-Ponzano、Vincenzo Aurilia、Gennaro Riccio、Bernard Henrissat、Pedro M. Coutinho、Andrea Strazzulli、Anna Padula、Maria Michela Corsaro、Giuseppina Pieretti、Gabriella Pocsfalvi、Immacolata Fiume、Raffaele Cannio、Mosè Rossi、Marco Moracci

  DOI：10.1074/jbc.m109.086470

  日期：2010.7

  SSO1353 operates via a retaining reaction mechanism. The catalytic nucleophile (Glu-335) was identified through trapping of the 2-deoxy-2-fluoroglucosyl enzyme intermediate and subsequent peptide mapping, while the general acid/base was identified as Asp-462 through detailed mechanistic analysis of a mutant at that position, including azide rescue experiments. SSO1353 has detectable homologs of unknown

  碳水化合物活性酶 (CAZymes) 是一大类酶，可构建和分解细胞的复杂碳水化合物。根据它们的氨基酸序列，它们被分类为显示保守催化机制、结构和活性位点残基的家族和氏族，但底物特异性可能不同。我们在这里报告了一种新型糖苷水解酶的鉴定和详细的分子表征，该酶由嗜热古菌 Sulfolobus solfataricus 的基因 sso1353 编码。该酶水解芳基 β-葡糖苷和 β-木糖苷，对转木糖基化反应产物的观察表明 SSO1353 通过保留反应机制起作用。催化亲核试剂 (Glu-335) 通过捕获 2-deoxy-2-fluoroglucosyl 酶中间体和随后的肽图鉴定，而一般酸/碱通过对该位置突变体的详细机理分析鉴定为 Asp-462 ，包括叠氮化物拯救实验。SSO1353 在古细菌、细菌和真核生物中具有可检测到的未知特异性的同源物，并且与非溶酶体胆汁酸 β-葡糖苷酶 GBA2（也称为葡糖脑
• Glycosynthase-Mediated Assembly of Xylanase Substrates and Inhibitors
  作者：Ethan D. Goddard-Borger、Brigitte Fiege、Emily M. Kwan、Stephen G. Withers

  DOI：10.1002/cbic.201100229

  日期：2011.7.25

  Assembly by synthase: An exo‐β‐xylosidase mutant with glycosynthase activity greatly simplifies the synthesis of xylanase substrates and inhibitors (see scheme). Some of these glycosynthase products were found to be the most potent competitive inhibitors of glycoside hydrolase family 10 and 11 xylanases reported to date.

  由合酶组装：具有糖合酶活性的exo - β-木糖苷酶突变体大大简化了木聚糖酶底物和抑制剂的合成（请参阅方案）。发现这些糖合酶产物中的一些是迄今为止报道的糖苷水解酶家族10和11木聚糖酶的最有效竞争抑制剂。
• Enzymatic transglycosylation of xylose using a glycosynthase
  作者：Young-Wan Kim、Hongming Chen、Stephen G. Withers

  DOI：10.1016/j.carres.2005.09.010

  日期：2005.12

  The application of the hyperactive glycosynthase derived from Agrobacterium sp. beta-glucosidase (AbgE358G-2F6) to the synthesis of xylo-oligosaccharides by using alpha-D-xylopyranosyl fluoride as donor represents the first successful use of glycosynthase technology for xylosyl transfer. Transfer to beta-nitrophenyl beta-D-glucopyranoside yields di- and trisaccharide products with beta-(1 -> 4) linkages in 63% and 35% yields, respectively. By contrast, transfer to p-nitrophenyl P-D-xylopyranoside yielded the beta-(1 -> 3) linked disaccharide and beta-D-Xyl-(1 -> 4)-beta-D-Xyl-(1 -> 3)-beta-D-Xyl-pNP as major products in 42% and 30% yields, respectively. Transfer of xylose to beta-D-Xyl-(1 -> 4)-beta-D-Xyl-pNP yielded the beta-(1 -> 4) linked trisaccharide in 98% yield, thereby indicating that transfers to xylo-disaccharides occur with formation of beta-(1 -> 4) bonds. Xylosylation of carbamate-protected deoxyxylonojirimycin produced a mixture of di- and tri-'saccharide' products in modest yields. (c) 2005 Elsevier Ltd. All rights reserved.
• Enzymatic synthesis of β-xylanase substrates: transglycosylation reactions of the β-xylosidase from Aspergillus sp.
  作者：Elena V Eneyskaya、Harry Brumer、Leon V Backinowsky、Dina R Ivanen、Anna A Kulminskaya、Konstantin A Shabalin、Kirill N Neustroev

  DOI：10.1016/s0008-6215(02)00467-6

  日期：2003.2

  A beta-D-xylosidase with molecular mass of 250 +/- 5 kDa consisting of two identical subunits was purified to homogeneity from a cultural filtrate of Aspergillus sp. The enzyme manifested high transglycosylation activity in transxylosylation with p-nitrophenyl P-D-xylopyranoside (PNP-X) as substrate, resulting in regio- and stereoselective synthesis of p-nitrophenyl (PNP) beta-(1 --> 4)-D-xylooligosaccharides with dp 2-7. All transfer products were isolated from the reaction mixtures by HPLC and their structures established by electrospray mass spectrometry and H-1 and C-13 NMR spectroscopy. The glycosides synthesised, beta-Xyl-1 --> (4-beta-Xyl-1 -->)(n)4-beta-Xyl-OC6H4NO2-p (n = 1 - 5), were tested as chromogenic substrates for family 10 beta-xylanase from Aspergillus orizae (XynA) and family 11 beta-xylanase I from Trichoderma reesei (XynT) by reversed-phase HPLC and UV-spectroscopy techniques. The action pattern of XynA against the foregoing PNP beta-(1 --> 4)-D-xylooligosaccharides differed from that of XynT in that the latter released PNP mainly from short PNP xylosides (dp 2 - 3) while the former liberated PNP from the entire set of substrates synthesised. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis of 2- and 4-nitrophenyl β-glycosides of β-(1 → 4)-d-xylo-oligosaccharides of dp 2–4
  作者：Kenichi Takeo、Yasushi Ohguchi、Rumi Hasegawa、Shinichi Kitamura

  DOI：10.1016/0008-6215(95)00214-e

  日期：1995.11

  synthesized by N-iodosuccinimide-silver triflate-promoted condensation using 11 and 15 as the glycosyl acceptors and ethyl 1-thio-β-d-xylopyranoside triacetate 16, 36, and 37 as the glycosyl donors. Also described are an improved preparation of 4 and 5, and the synthesis of 1-naphthyl β-d-xylopyranoside, as well as an alternative approach to the 2- and 4-nitrophenyl β-xylobiosides.

  通过二丁基氧化锡介导的酰化作用，将2-和4-硝基苯基β-d-吡喃吡喃糖苷（4和5）转化为相应的2,3-二-O-苯甲酰基衍生物11和15。炭柱色谱法，由市售材料制成，并转化为二糖和三糖甲基1-硫代-β-糖苷36和37。β-（1→4）-d-的2-和4-硝基苯基β-糖苷dp 2–4的木糖寡糖是通过N-碘代琥珀酰亚胺-三氟甲磺酸银促进的缩合反应合成的，使用11和15作为糖基受体，乙基1-硫代-β-d-吡喃吡喃糖苷三乙酸酯16、36和37作为糖基供体。 。还描述了改进的4和5的制备方法以及1-萘β-d-吡喃吡喃糖苷的合成，以及2-和4-硝基苯基β-吡喃二糖苷的替代方法。