Thermally induced substrate release via intramolecular cyclizations of Amino esters and Amino carbonates

Ralph J. Knipp, Rosendo Estrada, Palaniappan Sethu, Michael H. Nantz

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

The relative cleavage of an alcohol from a panel of amino esters and amino carbonates via intramolecular cyclization was examined as a mechanism for substrate release. Thermal stability at 37 °C was observed only for the seven-membered ring progenitors. Applicability of the approach was illustrated by δ-lactam formation within a poly(dimethylsiloxane) microchannel for release of a captured fluorescent probe.

Original languageEnglish (US)
Pages (from-to)3422-3429
Number of pages8
JournalTetrahedron
Volume70
Issue number21
DOIs
StatePublished - May 27 2014
Externally publishedYes

Fingerprint

Lactams
Carbonates
Cyclization
Microchannels
Fluorescent Dyes
Esters
Thermodynamic stability
Hot Temperature
Alcohols
Substrates
baysilon

Keywords

  • Drug delivery
  • Lactam
  • Oxazolidinone
  • Poly(dimethylsiloxane) microchannel

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Thermally induced substrate release via intramolecular cyclizations of Amino esters and Amino carbonates. / Knipp, Ralph J.; Estrada, Rosendo; Sethu, Palaniappan; Nantz, Michael H.

In: Tetrahedron, Vol. 70, No. 21, 27.05.2014, p. 3422-3429.

Research output: Contribution to journalArticle

Knipp, Ralph J. ; Estrada, Rosendo ; Sethu, Palaniappan ; Nantz, Michael H. / Thermally induced substrate release via intramolecular cyclizations of Amino esters and Amino carbonates. In: Tetrahedron. 2014 ; Vol. 70, No. 21. pp. 3422-3429.
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