4-nitrophenyl O-β-D-xylopyranosyl-(1<*>4)-bis4)>-β-D-xylopyranoside | 173468-35-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-nitrophenyl O-β-D-xylopyranosyl-(1<*>4)-bis4)>-β-D-xylopyranoside
• 英文别名: p-nitrophenyl β-D-xylopyranosyl-(1->4)-bis [β-D-xylopyranosyl-(1->4)]-β-D-xylopyranoside；4-nitrophenyl β-D-xylopyranosyl-(1->4)-bis[β-D-xylopyranosyl-(1->4)]-β-D-xylopyranoside；Xyl(b1-4)Xyl(b1-4)Xyl(b1-4)Xyl(b)-O-Ph(4-NO2)；(2S,3R,4S,5R)-2-[(3R,4R,5R,6S)-6-[(3R,4R,5R,6S)-6-[(3R,4R,5R,6S)-4,5-dihydroxy-6-(4-nitrophenoxy)oxan-3-yl]oxy-4,5-dihydroxyoxan-3-yl]oxy-4,5-dihydroxyoxan-3-yl]oxyoxane-3,4,5-triol
• CAS: 173468-35-4
• 化学式: C₂₆H₃₇NO₁₉
• 分子量: 667.575
• InChiKey: UBHVSAKUAWQUOO-QAIZBUEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.9
• 重原子数：
  46
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  302
• 氢给体数：
  9
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  4-nitrophenyl O-β-D-xylopyranosyl-(1<*>4)-bis4)>-β-D-xylopyranoside 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-4⁴-glucosyl-β-xylotetraoside
  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-nitrophenyl O-β-D-xylopyranosyl-(1<*>4)-bis4)>-β-D-xylopyranoside
  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

• 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。
• Novel substrates for the automated and manual assay of endo -1,4-β-xylanase
  作者：David Mangan、Claudio Cornaggia、Agnija Liadova、Niall McCormack、Ruth Ivory、Vincent A. McKie、Aaron Ormerod、Barry V. McCleary

  DOI：10.1016/j.carres.2017.02.009

  日期：2017.6

  reproducible, automatable assay for this enzyme that is based on the use of a chemically defined substrate has not been described to date. Reported herein is a new enzyme coupled assay procedure, termed the XylX6 assay, that employs a novel substrate, namely 4,6-O-(3-ketobutylidene)-4-nitrophenyl-β-45-O-glucosyl-xylopentaoside. The development of the substrate and associated assay is discussed here and

  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。