Solid-phase synthesis of polyfunctional polylysine dendrons using aldehyde linkers

Daniel K. Svenssen, Sahar Mirsharghi, Ulrik Boas

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

A straightforward method for the solid-phase synthesis of C-terminally modified polylysine dendrons has been developed by applying bisalkoxybenzaldehyde and trisalkoxybenzaldehyde linkers. The method has been used for the synthesis of polylysine dendrons with a variety of C-terminal ‘tail groups’ such as alkyl, propargyl, and dansyl to give dendrons in high crude purity. Furthermore, the method was successful for the synthesis of dendrons with multiple N-terminal pentapeptide groups together with C-terminal alkyl and propargyl tail groups. Finally, the method was shown to be well-suited for automated synthesis.
Original languageEnglish
JournalTetrahedron Letters
Volume55
Issue number29
Pages (from-to)3942-3945
Number of pages4
ISSN0040-4039
DOIs
Publication statusPublished - 2014

Keywords

  • Polylysine dendron
  • Solid-phase synthesis
  • Backbone amide linker
  • Polyfunctional

Cite this

Svenssen, Daniel K. ; Mirsharghi, Sahar ; Boas, Ulrik. / Solid-phase synthesis of polyfunctional polylysine dendrons using aldehyde linkers. In: Tetrahedron Letters. 2014 ; Vol. 55, No. 29. pp. 3942-3945.
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Solid-phase synthesis of polyfunctional polylysine dendrons using aldehyde linkers. / Svenssen, Daniel K.; Mirsharghi, Sahar; Boas, Ulrik.

In: Tetrahedron Letters, Vol. 55, No. 29, 2014, p. 3942-3945.

Research output: Contribution to journalJournal articleResearchpeer-review

TY - JOUR

T1 - Solid-phase synthesis of polyfunctional polylysine dendrons using aldehyde linkers

AU - Svenssen, Daniel K.

AU - Mirsharghi, Sahar

AU - Boas, Ulrik

PY - 2014

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N2 - A straightforward method for the solid-phase synthesis of C-terminally modified polylysine dendrons has been developed by applying bisalkoxybenzaldehyde and trisalkoxybenzaldehyde linkers. The method has been used for the synthesis of polylysine dendrons with a variety of C-terminal ‘tail groups’ such as alkyl, propargyl, and dansyl to give dendrons in high crude purity. Furthermore, the method was successful for the synthesis of dendrons with multiple N-terminal pentapeptide groups together with C-terminal alkyl and propargyl tail groups. Finally, the method was shown to be well-suited for automated synthesis.

AB - A straightforward method for the solid-phase synthesis of C-terminally modified polylysine dendrons has been developed by applying bisalkoxybenzaldehyde and trisalkoxybenzaldehyde linkers. The method has been used for the synthesis of polylysine dendrons with a variety of C-terminal ‘tail groups’ such as alkyl, propargyl, and dansyl to give dendrons in high crude purity. Furthermore, the method was successful for the synthesis of dendrons with multiple N-terminal pentapeptide groups together with C-terminal alkyl and propargyl tail groups. Finally, the method was shown to be well-suited for automated synthesis.

KW - Polylysine dendron

KW - Solid-phase synthesis

KW - Backbone amide linker

KW - Polyfunctional

U2 - 10.1016/j.tetlet.2014.04.127

DO - 10.1016/j.tetlet.2014.04.127

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JF - Tetrahedron Letters

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