5-fluoro-5-deoxyribose | 363-76-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-fluoro-5-deoxyribose
• 英文别名: FDR；5-fluoro-5-deoxy-D-ribose；D-ribo-5-Fluor-2,3,4-trihydroxy-valeraldehyd；5-Fluor-5-desoxy-D-ribose；5-Fluoro-5-deoxyribose；(2R,3S,4S)-5-fluoro-2,3,4-trihydroxypentanal
• CAS: 363-76-8
• 化学式: C₅H₉FO₄
• 分子量: 152.122
• InChiKey: APUXOCNWXSPZLI-MROZADKFSA-N

物化性质

• 沸点：
  335.7±32.0 °C(Predicted)
• 密度：
  1.415±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-fluoro-5-deoxyribose 、 乙酸酐 在 吡啶 作用下， 生成 1,2,3-tri-O-acetyl-5-deoxy-5-fluoro-β-D-ribofuranose
  参考文献：
  名称：

  5-Deoxy-5-fluoro-D-ribofuranosyl Derivatives of Certain Purines, Pyrimidines and 5,6-Dimethylbenzimidazole

  摘要：

  DOI：

  10.1021/ja01553a061
• 作为产物：
  描述：

  5’-三磷酸腺苷 在 potassium fluoride 、 L-蛋氨酸 、 Escherichia coli recombinant S-adenosyl-L-methionine synthase MetK 、 recombinant methylthioadenosine nucleosidase MtnN 、 Streptomyces cattleya NBRC₁₄₀₅₇ N-terminally His-tagged fluorinase 、 potassium chloride 、 magnesium chloride 作用下， 反应 24.0h， 生成 5-fluoro-5-deoxyribose
  参考文献：
  名称：

  One-pot three-step continuous enzymatic synthesis of 5-fluoro-5-deoxy-d-ribose

  摘要：

  The one-pot three-step continuous enzymatic synthesis of 5-fluoro-5-deoxy-D-ribose (5-FOR) from ATP and L-methionine using S-adenosyl-L-methionine synthase (MetK), fluorinase and methylthioadenosine nucleosidase (MtnN) in the presence of fluoride ion, was described. Especially, for the purpose of the sustainable development of fluorine chemistry, the reuse of fluoride ion generated from BF(4) ionic liquids and/or the biodegradation of BTF in the one-pot synthetic process to 5-FOR, was described. (C) 2011 Published by Elsevier B.V.

  DOI：

  10.1016/j.molcatb.2011.06.018

文献信息

• Efficient bioconjugation of 5-fluoro-5-deoxy-ribose (FDR) to RGD peptides for positron emission tomography (PET) imaging of αvβ3 integrin receptor
  作者：Sergio Dall'Angelo、Qingzhi Zhang、Ian N. Fleming、Monica Piras、Lutz F. Schweiger、David O'Hagan、Matteo Zanda

  DOI：10.1039/c3ob40550h

  日期：——

  The utility of 5-fluoro-5-deoxyribose (FDR) as an efficient bioconjugation agent for radiolabelling of the RGD peptides c(RGDfK) and c(RGDfC) is demonstrated. The bioconjugation is significantly superior to that achieved with 2-fluoro-2-deoxyglucose (FDG) and benefits from the location of the fluorine at C-5, and that ribose is a 5-membered ring sugar rather than a 6-membered ring. Both features favour ring opening to the aldehydic form of the sugar to promote smooth oxime ligation with aminooxy ether functionalised peptides. [18F]FDR was prepared in this study by synthesis from fluoride-18 using an automated synthesis protocol adapting that used routinely for [18F]FDG. c(RGDfK) was functionalised with an aminooxyacetyl group (Aoa) via its lysine terminus, while c(RGDfC) was functionalised with an aminooxyhexylmaleimide (Ahm) through a cysteine–maleimide conjugation. Bioconjugation of [18F]FDR to c(RGDfC)-Ahm proved to be more efficient than c(RGDfK)-Aoa (92% versus 65%). The unlabelled (19F) bioconjugates c(RGDfK)-Aoa-FDR and c(RGDfC)-Ahm-FDR were prepared and their in vitro affinity to purified integrin αvβ3 was determined. c(RGDfK)-Aoa-FDR showed the greater affinity. Purified “hot” bioconjugates c(RGDfK)-Aoa-[18F]FDR and c(RGDfC)-Ahm-[18F]FDR were assayed by incubation with MCF7, LNCaP and PC3 cell lines. In both cases the conjugated RGD peptides showed selectivity for PC3 cells, which express αvβ3 integrin, with the c(RGDfK)-Aoa-[18F]FDR demonstrating better binding, consistent with its higher in vitro affinity. The study demonstrates that [18F]FDR is an efficient bioconjugation ligand for RGD bioactive peptides.

  研究表明，5-氟-5-脱氧核糖（FDR）作为RGD肽c(RGDfK)和c(RGDfC)的放射标记高效生物偶联剂具有实用性。与2-氟-2-脱氧葡萄糖（FDG）相比，生物偶联效果显著优越，这得益于氟原子位于C-5位置，以及核糖是五元环糖而非六元环糖的特点。这两个特性有利于糖环开环形成醛式，促进与氨基氧乙基功能化肽的顺利肟连接。在本研究中，[18F]FDR通过从氟-18开始，采用适应常规[18F]FDG合成方法的自动化合成协议制备。c(RGDfK)通过其赖氨酸末端与氨基氧乙酰基（Aoa）功能化，而c(RGDfC)通过半胱氨酸-马来酰亚胺连接与氨基氧己基马来酰亚胺（Ahm）功能化。[18F]FDR与c(RGDfC)-Ahm的生物偶联证明比c(RGDfK)-Aoa更高效（92%对65%）。制备了未标记的（19F）生物偶联物c(RGDfK)-Aoa-FDR和c(RGDfC)-Ahm-FDR，并测定了它们对纯化整合素αvβ3的体外亲和力。c(RGDfK)-Aoa-FDR显示出更高的亲和力。纯化的“热”生物偶联物c(RGDfK)-Aoa-[18F]FDR和c(RGDfC)-Ahm-[18F]FDR通过与MCF7、LNCaP和PC3细胞系共孵育进行检测。两种情况下，结合的RGD肽均显示出对表达αvβ3整合素的PC3细胞的选择性，其中c(RGDfK)-Aoa-[18F]FDR显示出更好的结合效果，与其更高的体外亲和力一致。该研究表明，[18F]FDR是RGD生物活性肽的高效生物偶联配体。
• 168. Fluorocarbohydrates. Part I. The synthesis of 6-deoxy-6-fluoro-α-<scp>D</scp>-galactose and 5-deoxy-5-fluoro-αβ-<scp>D</scp>-ribose
  作者：N. F. Taylor、P. W. Kent

  DOI：10.1039/jr9580000872

  日期：——
• 5-Deoxy-5-fluoro-D-ribofuranosyl Derivatives of Certain Purines, Pyrimidines and 5,6-Dimethylbenzimidazole
  作者：Henry M. Kissman、Martin J. Weiss

  DOI：10.1021/ja01553a061

  日期：1958.10
• One-pot three-step continuous enzymatic synthesis of 5-fluoro-5-deoxy-d-ribose
  作者：Noritaka Iwai、Yuki Kitahara、Tomoya Kitazume

  DOI：10.1016/j.molcatb.2011.06.018

  日期：2011.12

  The one-pot three-step continuous enzymatic synthesis of 5-fluoro-5-deoxy-D-ribose (5-FOR) from ATP and L-methionine using S-adenosyl-L-methionine synthase (MetK), fluorinase and methylthioadenosine nucleosidase (MtnN) in the presence of fluoride ion, was described. Especially, for the purpose of the sustainable development of fluorine chemistry, the reuse of fluoride ion generated from BF(4) ionic liquids and/or the biodegradation of BTF in the one-pot synthetic process to 5-FOR, was described. (C) 2011 Published by Elsevier B.V.