2-bromoethyl β-D-galactopyranoside | 89983-40-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-bromoethyl β-D-galactopyranoside
• 英文别名: 2-bromoethyl β-D-galactoside；2-bromoethyl beta-D-galactopyranoside；(2R,3R,4S,5R,6R)-2-(2-bromoethoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 89983-40-4
• 化学式: C₈H₁₅BrO₆
• 分子量: 287.107
• InChiKey: BQGLYRBERUCSMN-DWOUCZDBSA-N

物化性质

• 沸点：
  479.0±45.0 °C(Predicted)
• 密度：
  1.77±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-bromoethyl β-D-galactopyranoside 在 zinc(II) chloride 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 2-bromoethyl 3-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranoside
  参考文献：
  名称：

  糖苷合成中的2-溴乙基糖苷：制备包含α-L-Fuc-（1 ---- 2）-D-Gal和β-D-Gal-（1 ---- 4）-D-GlcNAc的糖蛋白。

  摘要：

  α-L-Fuc-（1 ---- 2）-D-Gal和β-D-Gal-（1 ---- 4）糖苷的合成证明了2-溴乙基糖苷在碳水化合物合成中的适用性）-D-GlcNAc。溴乙基糖苷配基被转化成甲氧基羰基乙基硫基乙基间隔基，该间隔基允许糖与蛋白质（BSA和KLH）偶联。

  DOI：

  10.1016/0008-6215(84)85159-9
• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 2-bromoethyl β-D-galactopyranoside
  参考文献：
  名称：

  Glycodendriproteins:  A Synthetic Glycoprotein Mimic Enzyme with Branched Sugar-Display Potently Inhibits Bacterial Aggregation

  摘要：

  The continuing ability of bacteria to resist current antibiotic treatments highlights the need for alternative strategies for inhibiting their pathogenicity. Bacterial attachment is a major factor in infectivity and virulence. This key binding phase of bacteria to any potential host is mediated by adhesin proteins and so these present an attractive therapeutic target for antiinfective blocking strategies. However, the natural ligands to adhesins are large, typically complex molecules that are difficult to mimic with small molecules. We describe here a method that creates precise synthetic mimics of glycoproteins that are designed to bind adhesins. By using protein-degrading enzymes as the basis for these mimics we have created large-molecule protein ligands that inhibit aggregation of pathogenic bacteria at levels greater than a million-fold higher than small-molecule inhibitors of adhesins.

  DOI：

  10.1021/ja031698u

文献信息

• Development and optimization of a competitive binding assay for the galactophilic low affinity lectin LecA from Pseudomonas aeruginosa
  作者：Ines Joachim、Sebastian Rikker、Dirk Hauck、Daniela Ponader、Sophia Boden、Roman Sommer、Laura Hartmann、Alexander Titz

  DOI：10.1039/c6ob01313a

  日期：——

  chronic infections. The bacterial protein LecA, a C-type lectin, is a virulence factor and an integral component for biofilm formation. Inhibition of LecA with its carbohydrate ligands results in reduced biofilm mass, a potential Achilles heel for treatment. Here, we report the development and optimization of a fluorescence polarization-based competitive binding assay with LecA for application in screening

  革兰氏阴性菌铜绿假单胞菌的感染导致免疫受损的患者和囊性纤维化患者的高死亡率。病原体可以从浮游生物转变为生物膜，从而保护自己免受抗生素治疗并宿主免疫防御以建立慢性感染。细菌蛋白LecA，一种C型凝集素，是一种致病因子，是生物膜形成不可或缺的组成部分。LecA及其碳水化合物配体的抑制作用导致生物膜质量降低，这可能是治疗的潜在致命弱点。在这里，我们报告与LecA的荧光偏振为基础的竞争性结合测定法的发展和优化，用于筛选潜在的抑制剂。由于D的亲和力低对于LecA-半乳糖，优化荧光配体以减少测定中的蛋白质消耗。使用一组已知的LecA抑制剂验证了该测定，并获得了与已知K d值高度吻合的IC 50值。最后，我们采用了优化的检测方法来筛选合成的硫代半乳糖苷和天然血型抗原的集合，并报告它们的结构-活性关系。此外，我们评估了LecA的多价荧光测定探针，并报告了其在抑制测定中的适用性。
• Glycosides
  申请人：Svenska Sockerfabriks AB

  公开号：US04675392A1

  公开（公告）日：1987-06-23

  An O-glycoside having the general formula: (sugar).sub.n --O--(CH.sub.2).sub.m --Hal wherein Hal is chlorine, bromine or iodine, m is an integer of 2-20 inclusive and n is an integer of 1 to 10, inclusive, with the proviso that when n=1 and m=2, the aldose is different from glucose; An O-glycoside having the general formula: (sugar).sub.n --O--(CH.sub.2).sub.m --S--R--R' wherein n is an integer of from 1-10, inclusive, m is an integer of from 2-20, inclusive, R is selected from the group consisting of alkyl having at most 25 carbon atoms and aryl and R' is selected from the group consisting of H, CHO, CH(OR').sub.2, NO.sub.2, NH.sub.2, OH, SH, COOH, COOCH.sub.3, COOCH.sub.2 CH.sub.3, CONHNH.sub.2 and CON.sub.3, wherein R" is C.sub.1-4 -alkyl; A glycoconjugate having the general formula: (sugar).sub.n --O--(CH.sub.2).sub.m --S--R--R" wherein n is an integer of from 1-10, inclusive, m is an integer of from 2-20, inclusive, R is selected from the group consisting of alkyl having at most 25 carbon atoms and aryl and R" constitutes a carrier; A bi-dentate O-glycoside having the general formula: [(sugar).sub.n --O--(CH.sub.2).sub.m --S--.sub.2 R wherein m, n and R have the above meaning; and processes for their preparation.

  一种具有一般式的O-糖苷：(糖).sub.n --O--(CH.sub.2).sub.m --Hal，其中Hal是氯、溴或碘，m是2-20的整数，n是1到10的整数，但当n=1且m=2时，醛糖与葡萄糖不同；一种具有一般式的O-糖苷：(糖).sub.n --O--(CH.sub.2).sub.m --S--R--R'，其中n是1-10的整数，m是2-20的整数，R选自最多含有25个碳原子的烷基和芳基，R'选自H、CHO、CH(OR').sub.2、NO.sub.2、NH.sub.2、OH、SH、COOH、COOCH.sub.3、COOCH.sub.2 CH.sub.3、CONHNH.sub.2和CON.sub.3，其中R"是C.sub.1-4-烷基；一种具有一般式的糖共轭物：(糖).sub.n --O--(CH.sub.2).sub.m --S--R--R"，其中n是1-10的整数，m是2-20的整数，R选自最多含有25个碳原子的烷基和芳基，R"构成载体；一种具有一般式的双叉O-糖苷：[(糖).sub.n --O--(CH.sub.2).sub.m --S--.sub.2 R，其中m、n和R具有上述含义；以及它们的制备方法。
• Synthesis and use of glycodendrimer reagents
  申请人：——

  公开号：US20020019039A1

  公开（公告）日：2002-02-14

  The present invention relates to a chemically modified mutant protein including a cysteine residue substituted for a residue other than cysteine n a precursor protein, the substituted cysteine residue being subsequently modified by reacting the cysteine residue with a glycosylated thiosulfonate. Also a method of producing the chemically modified mutant protein is provided. The present invention also relates to a glycosylated methanethiosulfonate. Another aspect of the present invention is a method of modifying the functional characteristics of a protein including providing a protein and reacting the protein with a glycosylated methanethiosulfonate reagent under conditions effective to produce a glycoprotein with altered functional characteristics as compared to the protein. In addition, the present invention relates to methods of determining the structure-function relationships of chemically modified mutant proteins. The present invention also relates to synthetic methods for producing thio-glycoses, the thio-glycoses so produced, and to methods for producing glycodendrimer reagents.

  本发明涉及一种化学修饰的突变蛋白，其中包括将半胱氨酸残基替换为前体蛋白中的其他残基，所替换的半胱氨酸残基随后通过与糖基化硫代磺酸盐反应而被修饰。还提供了一种生产该化学修饰的突变蛋白的方法。本发明还涉及一种糖基化的甲烷硫代磺酸盐。本发明的另一个方面是一种修改蛋白的功能特性的方法，包括提供蛋白并将蛋白与糖基化的甲烷硫代磺酸盐试剂在有效条件下反应，以产生具有与蛋白相比改变的功能特性的糖蛋白。此外，本发明涉及确定化学修饰的突变蛋白的结构-功能关系的方法。本发明还涉及用于产生硫代糖的合成方法，以及所产生的硫代糖，以及用于产生糖基树状聚合物试剂的方法。
• Synthesis of new carbohydrate-containing cationic alkyl glycerolipids with antitumor activity
  作者：E. V. Shmendel、K. A. Perevoshchikova、D. K. Shishova、T. S. Kubasova、L. L. Tyutyunnik、M. A. Maslov、N. G. Morozova、A. A. Shtil

  DOI：10.1007/s11172-015-1055-7

  日期：2015.7

  New non-phosphorous carbohydrate-containing cationic alkyl glycerolipids bearing a ter- minal glycosyl moiety were synthesized. An approach used for the preparation of 2-O-ethyl-1-O-octadecyl-rac-glycerol allowed us to increase the yield of this key precursor by a factor of two. The carbohydrate-containing cationic alkyl glycerolipids induced tumor cell death and minimal damage to normal cells (in

  合成了带有末端糖基部分的新的含非磷碳水化合物的阳离子烷基甘油脂。一种用于制备 2-O-乙基-1-O-十八烷基-外消旋甘油的方法使我们能够将这种关键前体的产量提高两倍。含碳水化合物的阳离子烷基甘油脂可诱导肿瘤细胞死亡，并对正常细胞（特别是红细胞）造成的损害最小，这使得新化合物有望用于实际用途。
• CHEMICALLY MODIFIED PROTEINS WITH A CARBOHYDRATE MOIETY
  申请人：——

  公开号：US20010018200A1

  公开（公告）日：2001-08-30

  The present invention relates to a chemically modified mutant protein including a cysteine residue substituted for a residue other than cysteine in a precursor protein, the substituted cysteine residue being subsequently modified by reacting the cysteine residue with a glycosylated thiosulfonate. Also, a method of producing the chemically modified mutant protein is provided. The present invention also relates to a glycosylated methanethiosulfonate. Another aspect of the present invention is a method of modifying the functional characteristics of a protein including providing a protein and reacting the protein with a glycosylated methanethiosulfonate reagent under conditions effective to produce a glycoprotein with altered functional characteristics as compared to the protein. In addition, the present invention relates to methods of determining the structure-function relationships of chemically modified mutant proteins.

  本发明涉及一种化学修饰的突变蛋白，包括在前体蛋白中用半胱氨酸残基替换非半胱氨酸残基，然后通过将半胱氨酸残基与糖基化硫代磺酸盐反应来修饰替换的半胱氨酸残基。此外，本发明还提供了一种制备化学修饰的突变蛋白的方法。本发明还涉及一种糖基化的甲硫代磺酸盐。本发明的另一方面是一种修改蛋白质功能特性的方法，包括提供蛋白质并将蛋白质与糖基化的甲硫代磺酸盐试剂反应，在有效条件下产生与蛋白质相比具有改变功能特性的糖蛋白。此外，本发明还涉及确定化学修饰的突变蛋白的结构-功能关系的方法。