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A curious conformational property of 2-amino-4-thiazolyl-methoxyimino polymers exhibiting activity against HIV-1 reverse transcriptase

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Abstract

The polymer formed from degradation of third-generation cephalosporin antibacterials is an inhibitor of HIV-1 reverse transcriptase. The polymer has a (Z)-2-(methoxyimino)-N-(2-iminoethyl)acetamide backbone linking thiazolyl rings. We used molecular modeling to investigate the three-dimensional structure of the polymer. Oligomers were constructed by a Scheraga-type buildup procedure. Energy minimization calculations were performed by molecular mechanics using the MMFF force field. Helical conformations are formed by the polymer. The implications of this discovery are discussed in relation to biological activity.

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Acknowledgments

We thank Dr. Kelsey Forsythe for managing our departmental hardware and software infrastructure. We also thank the anonymous referees for very helpful comments.

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Authors and Affiliations

  1. Department of Chemistry and Chemical Biology, Indiana University-Purdue University Indianapolis, 402 North Blackford Street, Indianapolis, IN, 46202, USA

    Karolina A. Kill, Angela C. Smith, Tina Mizdalo, Emaa Hasan Al-Mahrouq,  Nidhi & Donald B. Boyd

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  1. Karolina A. Kill
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  2. Angela C. Smith
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  3. Tina Mizdalo
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  4. Emaa Hasan Al-Mahrouq
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  5. Nidhi
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  6. Donald B. Boyd
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Correspondence to Donald B. Boyd.

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Kill, K.A., Smith, A.C., Mizdalo, T. et al. A curious conformational property of 2-amino-4-thiazolyl-methoxyimino polymers exhibiting activity against HIV-1 reverse transcriptase. Struct Chem 23, 137–145 (2012). https://doi.org/10.1007/s11224-011-9853-5

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