Permanent URL to this publication: http://dx.doi.org/10.5167/uzh-12646
Jeremic, T; Linden, A; Heimgartner, H (2008). New 21- and 24-atom Aib-containing cyclopeptides. Journal of Peptide Science, 14(9):1051-1061.
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The synthesis of two Aib-containing cyclic octapeptides, cyclo(Leu-Aib-Phe-Aib-Gly-Aib-Phe-Aib) (1) and cyclo(Gly-Aib-Aib-Val-Aib-Leu-Aib-Phe) (2), and a cyclic heptapeptide cyclo(Gly-Aib-Val-Aib-Leu-Aib-Phe) (3), is described. The linear precursors of 1–3 were prepared using solution-phase techniques, and the cyclisation was also accomplished in solution. Among the coupling reagents examined in the final macrolactamisation step, PyAOP, HATU and DEPC/DEPBT efficiently yielded cyclised products. However, the success of the cyclisation was found to be dependent on the coupling reagent used. The two octapeptides 1 and 2 were obtained in much better yields (up to 63%) than the cycloheptapeptide 3 (30–37%). In addition, crystal-state conformational analysis of 2 was performed by X-ray crystallography. Six intramolecular hydrogen bonds stabilise the structure characterised by two consecutive type II /I β-turns, two consecutive type II/III β-turns, one γ -turn, and one inverse γ -turn.
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|Item Type:||Journal Article, refereed, original work|
|Communities & Collections:||07 Faculty of Science > Department of Chemistry|
|Dewey Decimal Classification:||540 Chemistry|
|Deposited On:||06 Feb 2009 10:46|
|Last Modified:||05 Apr 2016 12:57|
|Funders:||Swiss National Science Foundation (SNF), F. Hoffmann-La Roche AG, Basel|
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