2-氯-4-硝基苯基-beta-d-半乳糖吡喃糖苷 | 123706-60-5

• 物质功能分类: 生物化工 - 糖类化合物 - 单糖
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-氯-4-硝基苯基-beta-d-半乳糖吡喃糖苷
• 中文别名: 2-氯-4-硝基苯基-Β-D-吡喃半乳糖苷
• 英文名称: (2-chloro-4-nitrophenyl) β-D-galactopyranoside
• 英文别名: 2-chloro-4-nitrophenyl-β-D-galactopyranoside；2-Chloro-4-nitrophenyl-beta-D-galactopyranoside；(2S,3R,4S,5R,6R)-2-(2-chloro-4-nitrophenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 123706-60-5
• 化学式: C₁₂H₁₄ClNO₈
• mdl: MFCD00064018
• 分子量: 335.698
• InChiKey: PJCVBKZRKNFZOD-YBXAARCKSA-N

物化性质

• 熔点：
  211℃ (methanol )

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  145
• 氢给体数：
  4
• 氢受体数：
  8

安全信息

• 安全说明：
  S24/25
• 海关编码：
  2932999099
• 储存条件：
  2-8°C

制备方法与用途

溶解于甲醇

反应信息

• 作为反应物：
  描述：

  N-((2S,3R,4R,5R,6R)-2-Allyloxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-acetamide 、 2-氯-4-硝基苯基-beta-d-半乳糖吡喃糖苷 在 McIlvain buffer 作用下， 反应 50.0h， 以64%的产率得到allyl 2-acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis and evaluation of glycosyl donors with novel leaving groups for transglycosylations employing β-galactosidase from bovine testes

  摘要：

  Novel aryl beta-D-galactopyranosides were synthesized employing phase-transfer catalysis, and assayed as potential galactose donors in the presence of P-galactosidase from bovine testes using pNP-Gal as a reference. The aglycones were represented mainly by nitrophenols containing halogens, hydroxymethyl, aldehyde, carboxyl, ester or amino functions. An unusual intermolecular acetyl migration onto the benzylic alcohol group was observed during galactosylation of hydroxymethylnitrophenols. Pyridyl glycosides were obtained by reaction with the corresponding silver pyridinolates. Glycosides of halo-, hydroxymethyl- or methoxy-carbonyl-nitrophenols as leaving groups gave virtually the same yields of transglycosylation products. A minor increase was achieved with nitrosalicylaldehyde as leaving group, whereas carboxy or amino derivatives gave very low or no yield of the transglycosylation product. Commercially available donors such as resorufinyl and 4-methylumbelliferyl beta-D-galactopyranosides exhibited a lower transglycosylation potential than these novel pNP-Gal derivatives. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.10.014
• 作为产物：
  描述：

  2-氯-4-硝基苯酚 在 sodium methylate 、 potassium carbonate 作用下， 以 甲醇 、 氯仿 、 丙酮 为溶剂， 反应 72.0h， 生成 2-氯-4-硝基苯基-beta-d-半乳糖吡喃糖苷
  参考文献：
  名称：

  Synthesis, Characterization, Kinetic Parameters, and Diagnostic Application of a Sensitive Colorimetric Substrate for β-Galactosidase (2-Chloro-4-Nitrophenyl-β-D-Galactopyranoside)

  摘要：

  DOI：

  10.1006/bioo.1993.1024

文献信息

• Evaluating N-benzylgalactonoamidines as putative transition state analogs for β-galactoside hydrolysis
  作者：Qiu-Hua Fan、Susanne Striegler、Rebekah G. Langston、James D. Barnett

  DOI：10.1039/c4ob00153b

  日期：——

  Experimental evidence is provided for p-methylbenzyl-D-galactonoamidine to function as a true transition state analog for the enzymatic hydrolysis of aryl-β-D-galactopyranosides by β-galactosidase (A. oryzae). The compound exhibits inhibition constants in the low nanomolar concentration range (12–56 nM) for a selection of substrates. Along these lines, a streamlined synthetic method based on phase-transfer

  实验证据提供了一种用于p -methylbenzyl- d -galactonoamidine到功能如对芳基-β-的酶水解的真实过渡态类似物d通过β半乳糖苷酶（-galactopyranosides米曲霉）。对于选择的底物，该化合物在低纳摩尔浓度范围 (12–56 nM) 内表现出抑制常数。沿着这些思路，优化了基于相转移催化的简化合成方法，以提供所需的各种新型芳基-β - D-吡喃半乳糖苷。最后，证实了半乳糖脒在测定条件下的稳定性。
• E.coli and salmonella test kit
  申请人：Patel Chandravadan

  公开号：US20080248518A1

  公开（公告）日：2008-10-09

  A method for testing for the presence of bacteria in the field includes using a mixer and frother or a reagent to disrupt bacteria cells. A sample is collected from a source suspected to be contaminated by bacteria. A mixer and frother or similar mixer is used to mix the sample, or a reagent is added to the sample, to form an elute by disrupting bacteria cells present in the sample to expose bacteria enzymes. A reagent pad is immersed in the elute and then withdrawn from the elute, or a drop of the elute is deposited on a reagent pad. After a waiting period, the reagent pad is observed to determine if the bacteria is present in or on the source. The source may be a body of water, produce, prepared food, a food preparation area, or food processing equipment. The reagent is generally a lysis reagent.

  一种用于现场检测细菌存在的方法包括使用混合器和起泡剂或试剂来破坏细菌细胞。从怀疑被细菌污染的源收集样品。使用混合器和起泡剂或类似的混合器混合样品，或向样品中加入试剂以通过破坏样品中存在的细菌细胞形成洗脱物，以暴露细菌酶。将试剂垫浸入洗脱物中，然后从洗脱物中取出，或者在试剂垫上滴入一滴洗脱物。等待一段时间后，观察试剂垫以确定源中是否存在细菌。源可以是水体、农产品、制备食品、食品制备区域或食品加工设备。试剂通常是裂解试剂。
• GLYCOSYLTRANSFERASE REVERSIBILITY FOR SUGAR NUCLEOTIDE SYNTHESIS AND MICROSCALE SCANNING
  申请人：Thorson Jon S.

  公开号：US20130004979A1

  公开（公告）日：2013-01-03

  The present invention generally relates to materials and methods for exploiting glycosyltransferase reversibility for nucleotide diphosphate (NDP) sugar synthesis. The present invention provides engineered glycosyltransferase enzymes characterized by improved reaction reversibility and expanded sugar donor specificity as compared to corresponding non-mutated glycosyltransferase enzymes. Such reagents provide advantageous routes to NDP sugars for subsequent use in a variety of biomedical applications, including enzymatic and chemo-enzymatic glycorandomization.

  本发明一般涉及利用糖基转移酶可逆性合成核苷酸二磷酸（NDP）糖的材料和方法。本发明提供了改良反应可逆性并扩展糖供体特异性的工程糖基转移酶酶，与相应的非突变糖基转移酶酶相比，具有更好的反应可逆性和扩展的糖供体特异性。这些试剂提供了有利的NDP糖路线，用于随后在各种生物医学应用中使用，包括酶促和化学酶促糖随机化。
• Substrates for B-galactosidase
  申请人：Bayer Corporation

  公开号：EP0292169A2

  公开（公告）日：1988-11-23

  Compounds useful as substrates for β-galactosidase have the general formula wherein X is halogen, nitro or hydrogen; Y is halogen, lower alkyl or hydrogen; W is lower alkyl or hydrogen; and Z is nitro or the aromatic ring structure wherein a is lower alkyl or hydrogen; b is halogen or hydrogen; c is lower alkyl or hydrogen; and d is SO₃Na; with the proviso that X is not nitro when Y is hydrogen.

  可用作 β-半乳糖苷酶底物的化合物具有通式，其中 X 是卤素、硝基或氢；Y 是卤素、低级烷基或氢；W 是低级烷基或氢；Z 是硝基或芳香环结构，其中 a 是低级烷基或氢；b 是卤素或氢；c 是低级烷基或氢；d 是 SO₃Na；但当 Y 是氢时，X 不是硝基。
• Verfahren zur Erhöhung der enzymatischen Reaktivität von Beta-Galactosidase
  申请人：BOEHRINGER MANNHEIM GMBH

  公开号：EP0428137A1

  公开（公告）日：1991-05-22

  Zur Erhöhung der enzymatischen Reaktivität von β-Galactosida­se setzt man dem Reaktionsgemisch ein Azid, Rhodanid, Cyanat und/oder Thiosulfat zu.

  为了提高 β-半乳糖苷酶的酶反应活性，可在反应混合物中加入叠氮化物、罗丹酸盐、氰酸盐和/或硫代硫酸盐。