Micro-flowers changing to nano-bundle aggregates by translocation of the sugar moiety in Janus TA nucleosides

Hang Zhao; Shiliang He; Mingli Yang; Xiurong Guo; Guang Xin; Chaoyang Zhang; Ling Ye; Liangyin Chu; Zhihua Xing; Wen Huang; Qianming Chen; Yang He

doi:10.1039/c3cc41383g

Micro-flowers changing to nano-bundle aggregates by translocation of the sugar moiety in Janus TA nucleosides

Chem Commun (Camb). 2013 May 8;49(36):3742-4. doi: 10.1039/c3cc41383g. Epub 2013 Mar 14.

Authors

Hang Zhao¹, Shiliang He, Mingli Yang, Xiurong Guo, Guang Xin, Chaoyang Zhang, Ling Ye, Liangyin Chu, Zhihua Xing, Wen Huang, Qianming Chen, Yang He

Affiliation

¹ Laboratory of Ethnopharmacology, Institute for Nanobiomedical Technology and Membrane Biology, Regenerative Medicine Research Center, West China Hospital, West China Medical School, Sichuan University, Chengdu 610041, China.

PMID: 23493862
DOI: 10.1039/c3cc41383g

Abstract

We designed and synthesized the Janus-type TA nucleosides (1-3) by using a transglycosylation protocol. Surprisingly, the subtle translocation of the ribose from N8 to N1 by about 230 pm in space leads to the formation of entirely different shaped superstructures, micro-flowers for J-AT and nano-bundles for J-TA.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Glycosylation
Hydrogen Bonding
Nanostructures / chemistry*
Nanostructures / ultrastructure
Nucleosides / chemical synthesis
Nucleosides / chemistry*
Solvents / chemistry
Temperature
Tin Compounds / chemistry

Substances

Nucleosides
Solvents
Tin Compounds
stannous chloride