875680-91-4

Upstream product

• 875680-89-0 (R)-N¹-(o-nitrophenylsulfonyl)-N³-(tert-butyloxycarbonyl)-1,3-diaminobutane 
• 5394-18-3 2-(4-bromobutyl)isoindoline-1,3-dione 
• 170367-68-7 (2-cyano-1(R)-methylethyl)carbamic acid, 1,1-dimethylethyl ester 
• 170367-69-8 (3-amino-1(R)-methylpropyl)carbamic acid, 1,1-dimethylethyl ester 
• 5457-30-7 4-phthalimido-1-iodobutane 

Downstream Products

• 875680-93-6 (R)-N¹-phthaloyl-N⁵-(o-nitrophenylsulfonyl)-N⁸-acetyl-1,8-diamino-5-azanonane 

Relevant academic research and scientific papers

Synthesis of novel optical isomers of α-methylpolyamines

Earlier unknown (R)- and (S)-α-methylspermidine, (R)- and (S)-α-methylspermine, (R,R)-, (S,S)-, and (R,S)-α,ω-dimethylspermine were synthesized in gram scale from readily available (R)- and (S)-2-aminopropanols in high overall yields.

α-methyl polyamines: Efficient synthesis and tolerance studies in vivo and in vitro. First evidence for dormant stereospecificity of polyamine oxidase

Efficient syntheses of metabolically stable α-methylspermidine 1, α-methylspermine 2, and bis-α,α-methylated spermine 3 starting from ethyl 3-aminobutyrate are described. The biological tolerance for these compounds was tested in wild-type mice and transgenic mice carrying the metallothionein promoter-driven spermidine/spermine N1- acetyltransferase gene (MT-SSAT). The efficient substitution of natural polyamines by their derivatives was confirmed in vivo with the rats harboring the same MT-SSAT transgene and in vitro with the immortalized fibroblasts derived from these animals. Enantiomers of previously unknown 1-amino-8-acetamido-5-azanonane dihydrochloride 4 were synthesized starting from enantiomerically pure (R)- and (S)-alaninols. The studies with recombinant human polyamine oxidase (PAO) showed that PAO (usually splits achiral substrates) strongly favors the (R)-isomer of 4 that demonstrates for the first time that the enzyme has hidden potency for stereospecificity.