Enantioselective synthesis of (R)- and (S)-3-methylspermidines

• Published in: Russian journal of bioorganic chemistry Vol. 41; no. 5; pp. 548 - 553
• Main Authors: Khomutov, M. A., Keinanen, T. A., Hyvonen, M. T., Weisell, J., Vepsalainen, J., Alhonen, L., Kochetkov, S. N., Khomutov, A. R.
• Format: Journal Article
• Language: English
• Published: Moscow Pleiades Publishing 01-09-2015
• Subjects: Biochemistry; Biomedical and Life Sciences; Biomedicine; Bioorganic Chemistry; Life Sciences; Organic Chemistry; DU145 cells; R- and S-isomers of 3-MeSpd; spermidine/spermine-N; acetyl-transferase; spermidine analogues; deoxyhypusine synthase; polyamines
• ISSN: 1068-1620; 1608-330X
• DOI: 10.1134/S1068162015050064

Earlier unknown enantiomerically pure (
R
)- and (
S
)-1,8-diamino-3-methyl-4-azaoctane’s (3-MeSpd’s) were synthesized within 11 steps with high overall yields and optical purity starting from commercially available
R
- and
S
-isomers of
N
-Boc-2-aminopropanol-1. Application of
R
- and
S
-isomers of 3-MeSpd for the investigation of the stereospecificity of spermidine transporter and peculiarities of deoxyhypusine synthase reaction are discussed.