A new approach in the solid-phase synthesis of polyamine derivatives: construction of polyamine backbones from the center

A new and divergent approach for the solid-phase synthesis of polyamines and polyamine derivatives is shown. Monoprotected diamines are coupled to the Merrifield resin and alkylated at the resin-bound benzylic amine with masked ω-aminoalkyl groups. Selective deprotection of either of the two termina...

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Bibliographic Details
Published inTetrahedron Vol. 57; no. 37; pp. 7893 - 7898
Main Authors Manov, Nikolay, Bienz, Stefan
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 10.09.2001
Elsevier
Subjects
Chemistry
Chemistry, Organic
convergent
Merrifield resin
Physical Sciences
polyamine
Science & Technology
solid-phase synthesis
polyamine
Merrifield resin
solid-phase synthesis
convergent
STIMULATION
DDE
ANALOGS
SPERMINE
TOXIN HO-416B
PROTECTING GROUP
BIOLOGICAL EVALUATION
TRANSFER-RNA
B-DNA
BINDING
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Summary:A new and divergent approach for the solid-phase synthesis of polyamines and polyamine derivatives is shown. Monoprotected diamines are coupled to the Merrifield resin and alkylated at the resin-bound benzylic amine with masked ω-aminoalkyl groups. Selective deprotection of either of the two terminal amino functions allows the specific prolongation or derivatization of the resin-bound triamines at the two ends of the molecules. The alkylation of monoprotected diamines, attached to the Merrifield resin with masked ω-aminoalkyl electrophiles, opens a way for an independent modification of linear polyamines at the two terminal ends.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(01)00768-2