Synthesis and conformational analysis of methyl 3-amino-2,3-dideoxyhexopyranosiduronic acids, new sugar amino acids, and their diglycotides
- 作者：Dorota Tuwalska ; Joanna Sienkiewicz ; Beata Liberek
- 关键词：SAAs ; Configuration ; Conformation ; Stability ; Homodimeric glycotides
- 刊名：Carbohydrate Research
- 出版年：2008
- 期刊代码：15_00086215
- 类别：ch
- 出版时间：19 May 2008
- 卷：343
- 期：7
- 页码：1142-1152
- 文件大小：257 K
摘要
The synthesis of methyl 3-azido- and 3-amino-2,3-dideoxyhexopyranosiduronic acids and their methyl esters with the -
,β-d-arabino-, -,β-d-ribo, and -,β-l-lyxo configurations is presented. The conformations of the synthesized sugar amino acids and their precursors are discussed on the basis of 1H NMR data. The influence of the 5-carboxyl group on the pyranose ring conformation is assessed, and the bonding of the monosugar amino acids into dimeric glycotides, using conventional solution-phase peptide syntheses, is reported.
,β-d-arabino-, -,β-d-ribo, and -,β-l-lyxo configurations is presented. The conformations of the synthesized sugar amino acids and their precursors are discussed on the basis of 1H NMR data. The influence of the 5-carboxyl group on the pyranose ring conformation is assessed, and the bonding of the monosugar amino acids into dimeric glycotides, using conventional solution-phase peptide syntheses, is reported.