D-(1-13C)-galactose | 40010-55-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-(1-13C)-galactose
• 英文别名: 1-13C-D-galactose；[1-13C]galactose；D-Galactose-1-13C；(3R,4S,5R,6R)-6-(hydroxymethyl)(213C)oxane-2,3,4,5-tetrol
• CAS: 40010-55-7；40010-56-8；56746-22-6；60821-16-1；60821-17-2；60821-20-7；60821-21-8
• 化学式: C₆H₁₂O₆
• 分子量: 181.147
• InChiKey: WQZGKKKJIJFFOK-ZGYLHYIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  D-(1-13C)-galactose 在 sodium hydroxide 、 sodium azide 、 mercaptoethyl alcohol 、 DL-半胱氨酸 、 DL-dithiothreitol 、 Glc-1-P 、 HEPES buffer 、 芬硫磷 、 potassium chloride 、 phosphoenolpyruvic acid monopotassium salt 、 phosphoenolpyruvate trisodium salt 、 尿苷-5’-二磷酸 、 5’-三磷酸腺苷 、 magnesium chloride 、 manganese(ll) chloride 作用下， 反应 164.0h， 生成 NuUAcα2,3Galβ1,4GlcNAcβOallyl
  参考文献：
  名称：

  Ichikawa, Yoshitaka; Lin, Ying-Chih; Dumas, David P., Journal of the American Chemical Society, 1992, vol. 114, # 24, p. 9283 - 9298

  摘要：

  DOI：

文献信息

• Substrate-dependent chemoselective aldose–aldose and aldose–ketose isomerizations of carbohydrates promoted by a combination of calcium ion and monoamines
  作者：Tomoaki Tanase、Tomoyuki Takei、Masanobu Hidai、Shigenobu Yano

  DOI：10.1016/s0008-6215(01)00156-2

  日期：2001.7

  with the CaCl(2) system in CD(3)OD revealed that the C-2 epimerization proceeds via stereospecific rearrangement of the carbon skeleton, or 1,2-carbon shift, and ketose formation proceeds partially through an intramolecular hydrogen migration or 1,2-hydride shift and, in part, via an enediol intermediate. These simultaneous aldose-aldose and aldose-ketose isomerizations showed interesting substrate-dependent

  通过将各种金属离子与二胺，单胺和氨基醇结合使用，对C-2上醛糖的差向异构化进行了广泛的研究。醛基在碱金属或稀土金属离子（Ca（2 +），Sr（2 +），Pr（3+）或Ce（3+））和单胺的结合下在C-2上发生差向异构三乙胺。特别是，Ca（2 +）-三乙胺系统证明有效地促进了醛糖的酮糖-酮糖异构化以及C-2差向异构。使用D-（1-（13）C）葡萄糖和D-（1-（13）C）半乳糖与CaCl（2）系统在CD（3）OD中的13C NMR研究表明，C-2差向异构化是通过立体特异性进行的碳骨架的重排或1，2-碳移位和酮糖的形成部分通过分子内氢迁移或1，2-氢化物移位进行，部分通过烯二醇中间体进行。这些同时的醛糖-醛糖和醛糖-酮糖异构化显示出有趣的底物依赖性化学选择性。具有2,3-赤型构型的甘露糖型醛糖（D-甘露糖，D-lyxose和D-核糖）对C-2差向异构体和醛糖-酮糖异构化均显示出相当大的抗性，而葡萄糖型糖具有2
• Measurement of interglycosidic 3JCH coupling constants of selectively 13C labeled oligosaccharides by 2D J-resolved 1H NMR spectroscopy
  作者：Vince Pozsgay、Nese Sari、Bruce Coxon

  DOI：10.1016/s0008-6215(98)00047-0

  日期：1998.3

  oligosaccharide methyl glycoside derivative contains a 13C label at C-1. The interglycosidic coupling constants (3JCH) of these 13C nuclei with the H-3 nuclei of the adjacent 2-acetamido-2-deoxy-D-glucose residues have been measured by two-dimensional, J-resolved 1H NMR spectroscopy. The magnitudes of these coupling constants indicate that the trisaccharide is conformationally different to the higher oligosaccharide

  已经制备了痢疾志贺氏菌1型的O-特异性多糖的三糖，四糖和五糖片段，其中每个寡糖甲基糖苷衍生物的D-半乳糖残基在C-1处包含13C标记。这些13 C核与相邻的2-acetamido-2-deoxy-D-葡萄糖残基的H-3核之间的糖苷间偶联常数（3JCH）已通过二维J分辨1H NMR光谱法进行了测量。这些偶联常数的大小表明，三糖与较高的低聚糖同系物在构象上不同，这与先前对13 C化学位移和1 JCH值的研究一致。
• Observations on the activation of methyl thioglycosides by iodine and its interhalogen compounds
  作者：K.P.Ravindranathan Kartha、Peter Cura、Mahmoud Aloui、S.Kristy Readman、Trevor J Rutherford、Robert A Field

  DOI：10.1016/s0957-4166(99)00501-7

  日期：2000.2

  to be intermolecular, whereas the latter iodine–hexamethyldisilane-promoted epimerisation is intramolecular. Treatment of the same methyl thiogalactosides with iodine monobromide gives rise to the thermodynamically favoured α-glycosyl bromides, whereas reaction with iodine monochloride initially gives the kinetic β-glycosyl chlorides, which slowly epimerise to the thermodynamic α-linked products. Differences

  在没有受体醇的情况下用碘处理“武装”的甲基硫代半乳糖苷会导致巯基糖苷差向异构化，而对相应的“解除武装”的甲基硫代糖苷没有影响。相比之下，碘-六甲基乙硅烷（原位生成碘三甲基硅烷）引起“解除武装”的硫代糖苷的差向异构化，最终在延长的暴露时间产生相应的α-糖基碘化物。交叉实验表明，前者由碘促进的差向异构化是分子间的，而后者由碘-六甲基乙硅烷促进的差向异构化是分子内的。用一溴化碘处理相同的甲基硫代半乳糖苷会产生热力学上有利的α-糖基溴化物，而与一氯化碘的反应最初会生成动力学的β-糖基氯化物，慢慢地向热力学α-连接产物中差向异构化。I–I，I–Br和I–Cl激活硫糖苷的结果不同，这表明通过精心选择启动子可能会影响基于硫糖苷的糖基化反应的立体化学过程。
• Sugar Nucleotide Regeneration Beads (Superbeads):  A Versatile Tool for the Practical Synthesis of Oligosaccharides
  作者：Xi Chen、Jianwen Fang、Jianbo Zhang、Ziye Liu、Jun Shao、Przemyslaw Kowal、Peter Andreana、Peng George Wang

  DOI：10.1021/ja005738v

  日期：2001.3.1

  Peng George Wang* Department of Chemistry, Wayne State Uni Versity Detroit, Michigan 48202 Recei Ved October 27, 2000 Application of carbohydrates in modern medicine is limited by the high cost of synthesis of most biologically important glycoconjugates. It is generally recognized that glycosyltransferasecatalyzed glycosylation is one of the most practical approaches. 1

  Xi Chen、Jianwen Fang、Jianbo Zhang、Ziye Liu、Jun Shao、Przemyslaw Kowal、Peter Andreana 和 Peng George Wang* 密歇根州底特律韦恩州立大学化学系 48202 接收日期 2000 年 10 月 27 日 碳水化合物在现代医学中的应用受到大多数生物学上重要的糖缀合物的高成本合成的限制。人们普遍认为糖基转移酶催化的糖基化是最实用的方法之一。1
• Three-Bond C−O−C−C Spin-Coupling Constants in Carbohydrates:  Development of a Karplus Relationship
  作者：Bidisha Bose、Shikai Zhao、Roland Stenutz、Francis Cloran、Paul B. Bondo、Gail Bondo、Brian Hertz、Ian Carmichael、Anthony S. Serianni

  DOI：10.1021/ja981127f

  日期：1998.11.1

  A range of C-13-labeled carbohydrates containing C-O-C-C coupling pathways having different structures and dihedral angles has been prepared and used to identify structural factors affecting (3)J(COCC), especially those across the O-glycosidic Linkages of oligosaccharides. Model mono- and disaccharides were geometrically optimized using density functional methods, and scalar couplings involving carbon were calculated using a similar approach coupled with finite-field perturbation theory. Experimental and calculated (3)J(COCC) values were in close agreement, thus allowing use of the latter to better define the effect of carbohydrate structure on (3)J(COCC) magnitude. In addition to dihedral angle, the disposition of terminal electronegative substituents along the C-O-C-C coupling pathway significantly affects (3)J(COCC) values, and structural motifs have been identified where these effects may be encountered in oligosaccharides. A simple Karplus equation for trans-O-glycoside (3)J(COCC) values is proposed and has been applied in the reanalysis of trans-O-glycosidic couplings in C-13-labeled methyl beta-lactoside and sucrose. The behavior of trans-O-glycosidic (2)J(COC) and (3)J(COCH) values, which provide structural information complementary to that derived from (3)J(COCC) values, is also discussed.