TY  - CHAP
A1  - Selting, Margret
ED  - Fang, Mei
ED  - Li, Xianyin
T1  - Participants' practices of displaying affectivity in the construction of climaxes of complaint and amusing stories in talk-in-interaction
BT  - Interactional linguistic analyses and comparison
T2  - Interactional Linguistics and Chinese Language Studies, Vol. 3
Y1  - 2020
SP  - 29
EP  - 63
PB  - Language and Culture University Press
CY  - Beijing
ER  - 
TY  - JOUR
A1  - Wang, Xuebin
A1  - Wang, Xiaoli
A1  - Hu, Jing
A1  - Wang, Zhaoya
A1  - Pimpalpalle, Tukaram M.
A1  - Linker, Torsten
A1  - Yin, Jian
T1  - Study on the Synthesis of Novel Sugar Amino Acids
T1  - 新型糖氨基酸类化合物的合成研究
JF  - Acta chimica Sinica = Huaxue-xuebao
N2  - Sugar amino acids (SAAs) are carbohydrate derivatives bearing both amino and carboxylic acid functional groups. SAAs represent an important class of multifunctional building blocks, which are amenable to serve as glycomimetics or peptidomimetics with well-defined structures and useful properties. Because SAAs exist in nature in many forms with various biological activities, recently, many unnatural SAAs, as the demand for finding new molecules to discover new drugs and new materials, have been designed and synthesized by a number of research groups. In this paper, we have developed a convenient method for the synthesis of novel SAAs gluco-7 and galacto-7 for the first time. The structure of gluco-7 was similar to the natural SAA glucosaminuronic acid that was a component of many typical bacterial cell walls and could be used for the preparation of type D flu vaccine; while galacto-7 was similar to the natural SAA galactosaminuronic acid that was one of bacterial Vi-antigen components of Escherichia coli. Starting from unexpensive and commercially available 3,4,6-tri-O-acetyl-D-glucal and 3,4,6-tri-O-acetyl-D-galactal, two novel SAAs gluco-7 and galacto-7 were achieved in the linear 6 steps with 34% overall yield and 19% overall yield, respectively. The key reactions included radical addition, decarboxylation, iodine generation reaction, azide reaction and reductive amination reaction. The crucial step was the synthesis of the target compound gluco-7 from gluco-6. By using method A, the target compound gluco-7 was obtained in 4 steps with 63% overall yield. To optimize the transformation from gluco-6 to gluco-7, method B was developed to generate gluco-7 by using one-pot reaction successfully with 76% yield only in one step. It proved that method B was superior to method A with shorter steps and higher yields. All the new compounds were characterized by IR, H-1 NMR, C-13 NMR and HRMS data. Study on the synthesis and biological evaluation of linear and cyclic oligomers derived from gluco-7 and galacto-7 are currently in progress.
KW  - sugar amino acids
KW  - glycal
KW  - radical addition
KW  - one-pot reaction
KW  - synthesis
Y1  - 2015
U6  - https://doi.org/10.6023/A15030205
SN  - 0567-7351
VL  - 73
IS  - 7
SP  - 699
EP  - 704
PB  - Science China Press
CY  - Beijing
ER  -