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†

Hang Zhao,‡^ab Shiliang He,‡^a Mingli Yang,^c Xiurong Guo,^a Guang Xin,^a Chaoyang Zhang,^b Ling Ye,^b Liangyin Chu,^b Zhihua Xing,^a Wen Huang,*^a Qianming Chen*^b and Yang He*^a

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* Corresponding authors

^a 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
E-mail: heyangqx@scu.edu.cn, huangwen@scu.edu.cn

^b State Key Laboratory of Oral Diseases, West China Hospital of Stomatology, Sichuan University, No. 14, Section 3, Renminnan Road, Chengdu, Sichuan 610041, China
E-mail: qmchen@scu.edu.cn

^c Institute of Atomic and Molecular Physics, Sichuan University, Chengdu 610065, China

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.

Chemical Communications

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

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

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