3-Fluoroazetidinecarboxylic Acids and trans,trans-3,4-Difluoroproline as Peptide Scaffolds: Inhibition of Pancreatic Cancer Cell Growth by a Fluoroazetidine Iminosugar
文献类型：期刊论文
| 作者 | Liu, Zilei1; Jenkinson, Sarah F.1; Vermaas, Tom1; Adachi, Isao2; Wormald, Mark R.3; Hata, Yukako4; Kurashima, Yukiko4; Kaji, Akira4; Yu, Chu-Yi5,6; Kato, Atsushi2 |
| 刊名 | JOURNAL OF ORGANIC CHEMISTRY
 |
| 出版日期 | 2015-05-01 |
| 卷号 | 80期号:9页码:4244-4258 |
| 英文摘要 | Reverse aldol opening tenders amides of 3-hydroxyazetidinecarboxylic acids (3-OH-Aze) unstable above pH 8. Axe, found in sugar beet, is mis-incorporated for proline in peptides in humans and is associated with multiple sclerosis and teratogenesis. Axe-containing peptides may be oxygenated by prolyl hydroxylases resulting in potential damage of the protein by a reverse aldol of the hydroxyazetidine; this, rather than changes in conformation; may account for the deleterious effects of Axe. This paper describes the synthesis of 3-fluoro-Aze amino acids as hydroxy-Aze analogues which are not susceptible to aldol cleavage. 4-(Azidomethyl)-3-fluoro-Aze and 3,4-difluoroproline are new peptide building blocks. trans,trans-2,4-dihydroxy-3-fluoroazetidine, an iminosugar, inhibits the growth of pancreatic cancer cells to a similar degree as gemcitabine. |
| 收录类别 | SCI |
| 语种 | 英语 |
| 公开日期 | 2015-11-02 |
| 源URL | [http://ir.iccas.ac.cn/handle/121111/28081]  |
| 专题 | 化学研究所_分子识别与功能实验室 |
| 作者单位 | 1.Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England 2.Toyama Univ, Dept Hosp Pharm, Toyama 9300194, Japan 3.Univ Oxford, Dept Biochem, Glycobiol Inst, Oxford OX1 3QU, England 4.Hokuriku Univ, Fac Pharmaceut Sci, Kanazawa, Ishikawa 9201181, Japan 5.Chinese Acad Sci, Inst Chem, CAS Key Lab Mol Recognit & Funct, Beijing 100190, Peoples R China 6.Jiangxi Normal Univ, Natl Engn Res Ctr Carbohydrate Synth, Nanchang 330022, Peoples R China |
| 推荐引用方式 GB/T 7714 | Liu, Zilei,Jenkinson, Sarah F.,Vermaas, Tom,et al. 3-Fluoroazetidinecarboxylic Acids and trans,trans-3,4-Difluoroproline as Peptide Scaffolds: Inhibition of Pancreatic Cancer Cell Growth by a Fluoroazetidine Iminosugar[J]. JOURNAL OF ORGANIC CHEMISTRY,2015,80(9):4244-4258. |
| APA | Liu, Zilei.,Jenkinson, Sarah F..,Vermaas, Tom.,Adachi, Isao.,Wormald, Mark R..,...&Fleet, George W. J..(2015).3-Fluoroazetidinecarboxylic Acids and trans,trans-3,4-Difluoroproline as Peptide Scaffolds: Inhibition of Pancreatic Cancer Cell Growth by a Fluoroazetidine Iminosugar.JOURNAL OF ORGANIC CHEMISTRY,80(9),4244-4258. |
| MLA | Liu, Zilei,et al."3-Fluoroazetidinecarboxylic Acids and trans,trans-3,4-Difluoroproline as Peptide Scaffolds: Inhibition of Pancreatic Cancer Cell Growth by a Fluoroazetidine Iminosugar".JOURNAL OF ORGANIC CHEMISTRY 80.9(2015):4244-4258. |
入库方式： OAI收割
来源：化学研究所
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