S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-mercaptopropionic acid | 3254-10-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-mercaptopropionic acid
• 英文别名: 3-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosylthio)propionic acid；2,3,4,6-tetra-O-acetyl-1-S-mercaptopropionyl-β-D-glucose；1-S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-mercaptopropionate；3--propionsaeure；3-(Tetra-O-acetyl-β-D-glucopyranosylmercapto)-propionsaeure；3-[(2,3,4,6-Tetra-O-acetyl-b-D-glucopyranosyl)thio]-propanoic acid；3-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]sulfanylpropanoic acid
• CAS: 3254-10-2
• 化学式: C₁₇H₂₄O₁₁S
• 分子量: 436.437
• InChiKey: FGMXMRUEYSIRLE-CMZRPVNOSA-N

物化性质

• 沸点：
  544.1±50.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  29
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  177
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-mercaptopropionic acid 在 四(三苯基膦)钯 吗啉 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 67.34h， 生成 4-<(3,5-Bis<3-<3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylthio)propionamido>propoxy>benzamido)methyl>benzyl acrylate
  参考文献：
  名称：

  Dendronized polyacrylates with glucose units in the periphery

  摘要：

  报道了第一代（G-1）和第二代（G-2）树枝状构件（树枝）的合成，外围为乙酰保护的葡萄糖基团。这些树枝可以在焦点处选择性去保护，得到的羧酸随后与丙烯酸衍生物结合，生成树枝状的G-1和G-2大单体。它们的自由基引发聚合反应导致形成每个重复单元具有两个和四个表面葡萄糖单元的树枝状聚丙烯酸酯。

  DOI：

  10.1039/a808373h
• 作为产物：
  描述：

  1,2,3,4,6-alpha-D-葡萄糖五乙酸酯 、 3-巯基丙酸 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以86%的产率得到S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-mercaptopropionic acid
  参考文献：
  名称：

  Dendronized polyacrylates with glucose units in the periphery

  摘要：

  报道了第一代（G-1）和第二代（G-2）树枝状构件（树枝）的合成，外围为乙酰保护的葡萄糖基团。这些树枝可以在焦点处选择性去保护，得到的羧酸随后与丙烯酸衍生物结合，生成树枝状的G-1和G-2大单体。它们的自由基引发聚合反应导致形成每个重复单元具有两个和四个表面葡萄糖单元的树枝状聚丙烯酸酯。

  DOI：

  10.1039/a808373h

文献信息

• Lanthanide(<scp>III</scp>) Complexes of DOTA-Glycoconjugates: A Potential New Class of Lectin-Mediated Medical Imaging Agents
  作者：João P. André、Carlos F. G. C. Geraldes、José A. Martins、André E. Merbach、Maria I. M. Prata、Ana C. Santos、João J. P. de Lima、Éva Tóth

  DOI：10.1002/chem.200400187

  日期：2004.11.19

  The synthesis and characterization of a new class of DOTA (1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane) monoamide-linked glycoconjugates (glucose, lactose and galactose) of different valencies (mono, di and tetra) and their Sm(III), Eu(III) and Gd(III) complexes are reported. The 1H NMR spectrum of Eu(III)-DOTALac2 shows the predominance of a single structural isomer of square antiprismatic

  新型DOTA（1,4,7,10-四（羧甲基）-1,4,7,10-四氮杂环十二烷）单酰胺连接的糖价（葡萄糖，乳糖和半乳糖）连接的糖共轭物的合成与表征，二和四）及其Sm（III），Eu（III）和Gd（III）配合物。Eu（III）-DOTALac2的1H NMR谱图显示了DOTA螯合部分的方形反棱角几何结构的单个结构异构体的优势，并且绕着与靶向糖树状聚合物连接的酰胺键快速旋转。通过1H核磁弛豫分散液（NMRD）研究了Gd（III）-糖基共轭物的体外弛豫性，得出的参数接近于其他DOTA单酰胺所报道的参数。
• Cyclodextrin‐based carbohydrate clusters by amide bond formation
  作者：David A. Fulton、Anthony R. Pease、J. Fraser Stoddart

  DOI：10.1560/26tf-06hg-eqjj-w85j

  日期：2000.12

  Per‐6‐amino‐2,3‐dimethyl‐ß‐cyclodextrin was prepared very efficiently as its hydrochloride salt from native ß‐cyclodextrin in four steps and 89% overall yield. O‐Acetyl‐protected ß‐D‐thioglucose and ß‐D‐thiolactose derivatives, containing short spacer arms terminated with carboxylic acid functions, were prepared by the BF₃·OEt₂‐catalyzed thioglycosylation of ß‐D‐glucose pentaacetate and ß‐lactose octaacetate with 3‐mercaptopropionic acid, respectively. Utilizing amide bond formation as the key step, these thio‐ß‐D‐glucosyl and lactosyl derivatives were coupled to per‐6‐amino‐2,3‐dimethyl‐ß‐cyclodextrin to afford, after deprotection, perfunctionalized ß‐cyclodextrin‐based clusters containing seven thio‐ß‐D‐glucosyl and seven ß‐lactosyl appendages, respectively. Molecular modeling of both these ß‐cyclodextrin‐based clusters revealed the glucose and lactose clusters to be approximately 23 Å and 27 Å in diameter, respectively, and approximately 19 Å in height in both cases. The association constants for the complexation of the anti‐inflammatory drug naproxen by ß‐cyclodextrin, per‐2,3‐dimethyl‐ß‐cyclodextrin, and the lactose cluster of ß‐cyclodextrin in 0.01 M phosphate buffered saline solution (pH 7.4) were found by UV‐vis spectrophotometric titration to be 374 ± 75 M⁻¹, 351 ± 70 M⁻¹, and 165 ± 33 M⁻¹, respectively.

  摘要以原生ß-环糊精为原料，通过四个步骤高效地制备了Per-6-氨基-2,3-二甲基-ß-环糊精盐酸盐，总收率为89%。在 BF3-OEt2 催化下，ß-D-葡萄糖五乙酸酯和ß-乳糖八乙酸酯分别与 3-巯基丙酸发生硫代糖基化反应，制备出 O-乙酰基保护的ß-D-硫代葡萄糖和ß-D-硫代乳糖衍生物。以形成酰胺键为关键步骤，将这些硫代-ß-D-葡萄糖基和乳糖基衍生物与过-6-氨基-2,3-二甲基-ß-环糊精偶联，经脱保护后得到分别含有七个硫代-ß-D-葡萄糖基和七个ß-乳糖基附属物的全官能化ß-环糊精基团簇。对这两种ß-环糊精基团簇的分子建模显示，葡萄糖和乳糖团簇的直径分别约为 23 Å 和 27 Å，高度约为 19 Å。通过紫外可见分光光度滴定法发现，在 0.01 M 磷酸盐缓冲盐溶液（pH 7.4）中，ß-环糊精、过-2,3-二甲基ß-环糊精和ß-环糊精的乳糖簇与消炎药萘普生的络合常数分别为 374 ± 75 M-1、351 ± 70 M-1 和 165 ± 33 M-1。
• N-Terminal Sugar Conjugation and C-Terminal Thr-for-Thr(ol) Exchange in Radioiodinated Tyr³-octreotide:  Effect on Cellular Ligand Trafficking in Vitro and Tumor Accumulation in Vivo
  作者：Margret Schottelius、Jean Claude Reubi、Veronique Eltschinger、Markus Schwaiger、Hans-Jürgen Wester

  DOI：10.1021/jm040794i

  日期：2005.4.1

  For effective targeting of somatostatin receptor (sst) expressing tumors by radiolabeled octreotide analogues, high ligand uptake into sst-positive cells is mandatory. To optimize it, two modifications have been introduced into [I-125]Tyr(3)-octreotide ([I-125]TOC): C-terminal Thr-for-Thr(ol) exchange (leading to Tyr(3)-octreotate (TOCA)) and N-terminal derivatization with different carbohydrates. Both have significant impact on radioligand uptake into sst(2)-expressing cells in vitro and in vivo. Glucose conjugation via Amadori reaction by itself led to improved tumor uptake of [I-123] Gluc-TOC in vivo, which is based on an enhancement of peptide internalization despite a reduction in receptor affinity. In the case of the doubly modified analogues [I-123]Gluc-TOCA, [I-123]Gluc-S-TOCA, and [I-123] Gal-S-TOCA, a cumulative effect of both structural modifications was observed, leading up to a 5-fold increased uptake of these compounds in sst-expressing tumors compared to [I-125]TOC. Thus, glycosylation with small carbohydrates was found to be a suitable tool to enhance receptor-mediated uptake of radiolabeled octreotide analogues into sst-positive malignancies, leading to tracers with excellent characteristics for in vivo sst-imaging applications.
• Nokwequ, Mbulelo G.; Nkambule, Comfort M.; Gammon, David W., South African Journal of Chemistry, 2014, vol. 67, p. 180 - 183
  作者：Nokwequ, Mbulelo G.、Nkambule, Comfort M.、Gammon, David W.

  DOI：——

  日期：——