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Chemistry. 2018 Oct 17;24(58):15495-15501. doi: 10.1002/chem.201803429. Epub 2018 Sep 16.

Supermacrocyclic Assemblies by Hydrogen-Bond Codes of C7-Phenol Pyrazolo and Pyrrolo Derivatives of Adenine.

Author information

1
Department of Respiratory and Critical Care Medicine, Targeted Tracer Research and Development Laboratory, West China Hospital, Sichuan University, Chengdu, Sichuan, 610041, P. R. China.
2
Institute for Nanobiomedical Technology and Membrane Biology, Sichuan University, Chengdu, Sichuan, 610041, P. R. China.
3
School of Chemical Engineering, Sichuan University, Chengdu, Sichuan, 610041, P. R. China.

Abstract

Hydrogen bond (HB) mediated base pair motifs are versatile scaffolds of diverse supramolecular constructs. Here, we report that two new four- and six-membered supermacrocyclic assemblies with intriguing geometries could self-assemble from two new adenine derivatives, APN (1) and APC (2). The conversion of a conventional HB acceptor, N8 of 1, to a non-conventional HB donor, C8-H of 2, had a pronounced impact on the overall intricate HB network and self-assembly patterns, epitomizing the subtleties in design and exploitation of such base-pair motifs as promising tectons for building supramolecular architectures.

KEYWORDS:

nucleobases; pyrazolo[3,4-d]pyrimidine; pyrrolo[2,3-d]pyrimidine; self-assembly; supermacrocyclic assembly

PMID:
30109751
DOI:
10.1002/chem.201803429

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