2-脱氧-2-氟-d-赖氨酸 | 7226-39-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-脱氧-2-氟-d-赖氨酸
• 中文别名: 2-氟-alfa-d-2-脱氧-葡萄糖
• 英文名称: 2-deoxy-2-fluoro-D-mannopyranoside
• 英文别名: 2-deoxy-2-fluoro-D-mannopyranose；2-deoxy-2-fluoro-D-mannose；2F-Man；(3S,4S,5S,6R)-3-fluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-2,4,5-triol；2-deoxy-2-fluro-D-mannose；(3S,4S,5S,6R)-3-fluoro-6-(hydroxymethyl)oxane-2,4,5-triol
• CAS: 7226-39-3；7241-17-0；28876-44-0；38711-37-4；55449-80-4；62182-10-9；62182-14-3；86783-82-6；98856-44-1；98856-45-2；98856-46-3；31077-88-0
• 化学式: C₆H₁₁FO₅
• 分子量: 182.149
• InChiKey: ZCXUVYAZINUVJD-CBPJZXOFSA-N

物化性质

• 熔点：
  123-128

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 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：
  90.2
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-脱氧-2-氟-d-赖氨酸 在 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 Phosphoric acid dibenzyl ester (2R,4aR,6R,7S,8S,8aS)-7-fluoro-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl ester
  参考文献：
  名称：

  脂质A的氟化类似物的合成

  摘要：

  为了研究脂质A衍生物的构效关系，合成了一系列脂质X的氟化类似物。随后，使用脂质A合酶将它们酶促转化为相应的盘硬脂酸脂质A类似物。这进一步证明了该酶的低底物特异性。

  DOI：

  10.1016/s0040-4039(00)91596-x
• 作为产物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-deoxy-2-fluoro-α-D-mannopyranose 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以100%的产率得到2-脱氧-2-氟-d-赖氨酸
  参考文献：
  名称：

  脂质A的氟化类似物的合成

  摘要：

  为了研究脂质A衍生物的构效关系，合成了一系列脂质X的氟化类似物。随后，使用脂质A合酶将它们酶促转化为相应的盘硬脂酸脂质A类似物。这进一步证明了该酶的低底物特异性。

  DOI：

  10.1016/s0040-4039(00)91596-x

文献信息

• Efficient one-pot multienzyme synthesis of UDP-sugars using a promiscuous UDP-sugar pyrophosphorylase from Bifidobacterium longum (BLUSP)
  作者：Musleh M. Muthana、Jingyao Qu、Yanhong Li、Lei Zhang、Hai Yu、Li Ding、Hamed Malekan、Xi Chen

  DOI：10.1039/c2cc17577k

  日期：——

  A promiscuous UDP-sugar pyrophosphorylase (BLUSP) was cloned from Bifidobacterium longum strain ATCC55813 and used efficiently with a Pasteurella multocida inorganic pyrophosphatase (PmPpA) with or without a monosaccharide 1-kinase for one-pot multienzyme synthesis of UDP-galactose, UDP-glucose, UDP-mannose, and their derivatives. Further chemical diversification of a UDP-mannose derivative resulted in the formation of UDP-N-acetylmannosamine.

  从双歧杆菌（Bifidobacterium longum）ATCC55813株中克隆得到一种非特异的UDP-糖焦磷酸化酶（BLUSP），并将其与巴氏杆菌（Pasteurella multocida）的无机焦磷酸酶（PmPpA）有效配合使用，无论是否加入单糖1-激酶，都能实现UDP-半乳糖、UDP-葡萄糖、UDP-甘露糖及其衍生物的一锅法多酶合成。进一步对UDP-甘露糖衍生物进行化学修饰，形成了UDP-N-乙酰甘露糖胺。
• Metabolic pathway of 2-deoxy-2-fluoro-D-glucose and 2-deoxy-2-fluoro-D-mannose in mice bearing sarcoma 180 studied by fluorin-19 nuclear magnetic resonance.
  作者：MASAHARU KOJIMA、SATORU KURIBAYASHI、YOKO KANAZAWA、TERUSHI HARADAHIRA、YOSHIHIKO MAEHARA、HIDEYA ENDO

  DOI：10.1248/cpb.36.1194

  日期：——

  The metabolic products of 2-deoxy-2-fluoro-D-glucose (FDG) and 2-deoxy-2-fluoro-D-mannose (FDM) in sarcoma 180 cells transplanted in mice were investigated by fluorin-19 nuclear magnetic resonance (19F-NMR) spectroscopy. It became apparent that the administered FDG was converted to FDM (and/or FDM-6-phosphate) in tumor cells, and also the administered FDM was converted to FDG (and/or FDG-6-phosphate). At 9h after administration of FDM, the ratio of FDG (and/or FDG-6-phosphate) and FDM (and/or FDM-6-phosphate) reached equilibrium. On the other hand, it took more than 48h in the case of FDG administration. The equilibrium amount of FDM (and/or FDM-6-phosphate) was approximately four times as much as that of FDG (and/or FDG-6-phosphate) in both cases.

  通过氟-19核磁共振（19F-NMR）光谱研究了在小鼠体内移植的肉瘤180细胞中2-脱氧-2-氟-D-葡萄糖（FDG）和2-脱氧-2-氟-D-甘露糖（FDM）的代谢产物。结果表明，所施用的FDG在肿瘤细胞中转化为FDM（和/或FDM-6-磷酸），施用的FDM也转化为FDG（和/或FDG-6-磷酸）。施用FDM后9小时，FDG（和/或FDG-6-磷酸）与FDM（和/或FDM-6-磷酸）的比例达到平衡。另一方面，施用FDG后需要超过48小时。在这两种情况下，FDM（和/或FDM-6-磷酸）的平衡量大约是FDG（和/或FDG-6-磷酸）的四倍。
• A New Method for the Synthesis of Fluoro-Carbohydrates and Glycosides Using Selectfluor
  作者：Michael D. Burkart、Zhiyuan Zhang、Shang-Cheng Hung、Chi-Huey Wong

  DOI：10.1021/ja9723904

  日期：1997.12.1

  This paper describes a high-yield, one-step synthesis of 2-deoxy-2-fluoro sugars and their glycosides from glycals using the available electrophilic fluorination reagent 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor) in the presence of a nucleophile. The method was further expanded to the synthesis of glycosyl fluorides and glycosides from anomeric hydroxy

  本文描述了使用现有的亲电氟化试剂 1-氯甲基-4-氟-1,4-二氮杂二环[2.2.2] 从糖醛中高产、一步合成 2-脱氧-2-氟糖及其糖苷的方法辛烷双（四氟硼酸盐）（Selectfluor）在亲核试剂存在下。该方法进一步扩展到从异头羟基或硫糖苷衍生物合成糖基氟和糖苷。
• Synthesis of 2-deoxy-2-fluoro-D-mannose using fluoride ion.
  作者：TERUSHI HARADAHIRA、MINORU MAEDA、HIROKO OMAE、YUJI YANO、MASAHARU KOJIMA

  DOI：10.1248/cpb.32.4758

  日期：——

  Nucleophilic displacement reactions of the 3-O-methyl, and 3-O-benzyl derivatives (5, 11, and 12) of methyl 4, 6-O-benzylidene-2-O-(trifluoromethanesulfonyl)-β-D-glucopyranoside with tetraalkylammonium fluorides in acetonitrile proceeded smoothly to give, with inversion of configuration at C2, the corresponding methyl 2-deoxy-2-fluoro-β-D-mannopyranosides in good yields. Similar treatment of methyl 3-O-benzyl-4, 6-O-benzylidene-2-O-(trifluoromethanesulfonyl)-α-D-glucopyranoside (3) or methyl 3, 4, 6-tri-O-acetyl-2-O-(trifluoromethanesulfonyl)-β-D-glucopyranoside (8) resulted in decreased yield of the fluoro-manno compound. Efficient conversion of these fluorinated intermediates into 2-deoxy-2-fluoro-D-mannose (1) was achieved by heating with acidic reagents. These synthetic sequences could be easily adapted for the preparation of the 18F-labeled analog of 2-deoxy-2-fluoro-D-mannose (1).

  3-O-甲基和3-O-苄基衍生物（5、11和12）与四烷基铵氟化物在乙腈中的亲核取代反应顺利进行，在C2位反转构型，得到了相应的甲基2-脱氧-2-氟-β-D-甘露糖苷，产率良好。类似地，对甲基3-O-苄基-4,6-O-苄腈-2-O-(三氟甲磺酰)-α-D-葡萄糖苷（3）或甲基3,4,6-三-O-乙酰-2-O-(三氟甲磺酰)-β-D-葡萄糖苷（8）的处理导致氟化甘露化合物的产率降低。通过与酸性试剂加热，成功地将这些氟化中间体转化为2-脱氧-2-氟-D-甘露糖（1）。这些合成路线可以很容易地适应于制备标记有18F的2-脱氧-2-氟-D-甘露糖（1）类似物。
• Sialidase substrate specificity studies using chemoenzymatically synthesized sialosides containing C5-modified sialic acids
  作者：Hongzhi Cao、Yanhong Li、Kam Lau、Saddam Muthana、Hai Yu、Jiansong Cheng、Harshal A. Chokhawala、Go Sugiarto、Lei Zhang、Xi Chen

  DOI：10.1039/b916305k

  日期：——

  para-Nitrophenol-tagged sialyl galactosides containing sialic acid derivatives in which the C5 hydroxyl group of sialic acids was systematically substituted with a hydrogen, a fluorine, a methoxyl or an azido group were successfully synthesized using an efficient chemoenzymatic approach. These compounds were used as valuable probes in high-throughput screening assays to study the importance of the C5 hydroxyl group of sialic acid in the recognition and the cleavage of sialoside substrates by bacterial sialidases.

  成功合成了标记有对硝基苯酚的含唾液酸衍生物的唾液酸半乳糖苷，这些衍生物中唾液酸的C5羟基以氢、氟、甲氧基或叠氮基进行了系统性的替代，采用了一种高效的化学酶法。这些化合物作为宝贵的探针，用于高通量筛选实验，研究了唾液酸C5羟基在细菌唾液酶识别和切割唾液苷底物中的重要性。