Novel hydroxylamine-containing analogues of 1-guanidino-7-aminoheptane (GC7), an effective inhibitor of deoxyhypusine synthase

• Published in: Russian journal of bioorganic chemistry Vol. 42; no. 4; pp. 415 - 422
• Main Authors: Khomutov, M. A., Simonian, A. R., Weisell, J., Vepsalainen, J., Kochetkov, S. N., Khomutov, A. R.
• Format: Journal Article
• Language: English
• Published: Moscow Pleiades Publishing 01-07-2016
• Subjects: Biochemistry; Biomedical and Life Sciences; Biomedicine; Bioorganic Chemistry; Life Sciences; Organic Chemistry; alkoxyguanidines; inhibitors; O-substituted hydroxylamines; deoxyhypusine synthase; polyamines; GC7 analogues
• ISSN: 1068-1620; 1608-330X
• DOI: 10.1134/S1068162016040099

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.