Novel hydroxylamine-containing analogues of 1-guanidino-7-aminoheptane (GC7), an effective inhibitor of deoxyhypusine synthase
Earlier unknown hydroxylamine-containing analogues of 1-guanidino-7-aminohepane (GC7) containing the free aminooxy group (1-aminooxy-6-guanidinohexane), bis-guanyl derivatives of 1-aminooxy-6-aminohexane, and 1-aminooxy-5-aminopentane, and mono-guanidinooxy analogue (1-guanidinooxy-6-aminohexane) we...
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| Published in: | Russian journal of bioorganic chemistry Vol. 42; no. 4; pp. 415 - 422 |
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| Main Authors: | , , , , , |
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01-07-2016
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| Abstract | Earlier unknown hydroxylamine-containing analogues of 1-guanidino-7-aminohepane (GC7) containing the free aminooxy group (1-aminooxy-6-guanidinohexane), bis-guanyl derivatives of 1-aminooxy-6-aminohexane, and 1-aminooxy-5-aminopentane, and mono-guanidinooxy analogue (1-guanidinooxy-6-aminohexane) were synthesized in high overall yields from commercially available 5-(Boc-amino)1-pentanol and 6-(Boc-amino)-1-hexanol. It was demonstrated that 1,3-di-Boc-2-(trifluoromethylsulfonyl)guanidine is able to specifically amidinate the amino group in the presence of the free aminooxy group. The application of newly synthesized GC7 analogues for the investigation of the peculiarities of their interaction with the active site of deoxyhypusine synthase was discussed. |
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| AbstractList | Earlier unknown hydroxylamine-containing analogues of 1-guanidino-7-aminohepane (GC7) containing the free aminooxy group (1-aminooxy-6-guanidinohexane), bis-guanyl derivatives of 1-aminooxy-6-aminohexane, and 1-aminooxy-5-aminopentane, and mono-guanidinooxy analogue (1-guanidinooxy-6-aminohexane) were synthesized in high overall yields from commercially available 5-(Boc-amino)1-pentanol and 6-(Boc-amino)-1-hexanol. It was demonstrated that 1,3-di-Boc-2-(trifluoromethylsulfonyl)guanidine is able to specifically amidinate the amino group in the presence of the free aminooxy group. The application of newly synthesized GC7 analogues for the investigation of the peculiarities of their interaction with the active site of deoxyhypusine synthase was discussed. |
| Author | Kochetkov, S. N. Khomutov, A. R. Vepsalainen, J. Simonian, A. R. Weisell, J. Khomutov, M. A. |
| Author_xml | – sequence: 1 givenname: M. A. surname: Khomutov fullname: Khomutov, M. A. organization: Engelhardt Institute of Molecular Biology, Russian Academy of Sciences – sequence: 2 givenname: A. R. surname: Simonian fullname: Simonian, A. R. organization: Engelhardt Institute of Molecular Biology, Russian Academy of Sciences – sequence: 3 givenname: J. surname: Weisell fullname: Weisell, J. organization: School of Pharmacy, University of Eastern Finland – sequence: 4 givenname: J. surname: Vepsalainen fullname: Vepsalainen, J. organization: School of Pharmacy, University of Eastern Finland – sequence: 5 givenname: S. N. surname: Kochetkov fullname: Kochetkov, S. N. organization: Engelhardt Institute of Molecular Biology, Russian Academy of Sciences – sequence: 6 givenname: A. R. surname: Khomutov fullname: Khomutov, A. R. email: alexkhom@list.ru organization: Engelhardt Institute of Molecular Biology, Russian Academy of Sciences |
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| Keywords | alkoxyguanidines inhibitors O-substituted hydroxylamines deoxyhypusine synthase polyamines GC7 analogues |
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| Title | Novel hydroxylamine-containing analogues of 1-guanidino-7-aminoheptane (GC7), an effective inhibitor of deoxyhypusine synthase |
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