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Synthesis of a 6,6-Spiroketal Amino Acid and Its Incorporation into a Peptide Turn Sequence Using Solid-Phase Peptide Synthesis


Kueh, J T B; Choi, K W; Williams, G M; Moehle, K; Bacsa, B; Robinson, J A; Brimble, M A (2013). Synthesis of a 6,6-Spiroketal Amino Acid and Its Incorporation into a Peptide Turn Sequence Using Solid-Phase Peptide Synthesis. Chemistry - A European Journal, 19(12):3807-3811.

Abstract

The rigid structure of an anomerically stabilised spiroketal motif enables the appendage of substituents in a fixed conformation. To assess the ability of a spiroketal motif to induce a turn structure and participate in solid-phase peptide synthesis (SPPS), an Fmoc-spiroketal amino acid was synthesised and incorporated into a spiroketal-containing cyclic peptide (see figure).

Abstract

The rigid structure of an anomerically stabilised spiroketal motif enables the appendage of substituents in a fixed conformation. To assess the ability of a spiroketal motif to induce a turn structure and participate in solid-phase peptide synthesis (SPPS), an Fmoc-spiroketal amino acid was synthesised and incorporated into a spiroketal-containing cyclic peptide (see figure).

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3 citations in Web of Science®
3 citations in Scopus®
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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:18 March 2013
Deposited On:08 Jan 2014 11:38
Last Modified:08 Dec 2017 01:44
Publisher:Wiley-VCH Verlag Berlin
ISSN:0947-6539
Publisher DOI:https://doi.org/10.1002/chem.201204546
PubMed ID:23424080

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