Automated solid-phase synthesis and structural investigation of -peptidosulfonamides and -peptidosulfonamide/-peptide hybrids: -peptidosulfonamide and -peptide foldamers are two of a different kind

de Jong, R., Rijkers, D.T.S. and Liskamp, R.M.J. (2002) Automated solid-phase synthesis and structural investigation of -peptidosulfonamides and -peptidosulfonamide/-peptide hybrids: -peptidosulfonamide and -peptide foldamers are two of a different kind. Helvetica Chimica Acta, 85(12), pp. 4230-4243. (doi:10.1002/hlca.200290008)

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Abstract

Fmoc-protected β-aminoethane sulfonylchlorides can be employed for efficient automated solid phase synthesis of β-peptidosulfonamides and β-peptidosulfonamide/β-peptide hybrids containing one or more β-peptidosulfonamide residues. Thus, Fmoc-protected β-aminoethane sulfonylchlorides 5a–c led to the hexa-β-peptidosulfonamide 9 and the nona-β-peptidosulfonamide 10. In addition, the β-peptidosulfonamide/β-peptide hybrids 13 and 16, consisting of six and nine β-residues, respectively, and containing a single β-peptidosulfonamide unit in the middle, as well as the peptidosulfonamide/β-peptide hybrid 15 with nine β-residues, including an N-terminal β-peptidosulfonamide residue, were synthesized by automated solid-phase synthesis. Both CD and NMR spectroscopic measurements did not indicate any helical secondary structure for 9 and 10. As was shown by CD-measurements, the β-peptidosulfonamide residue in the hybrids 13, 15, and 16 acts as a ‘helix breaker', especially when located in the middle of the hybrid chain (13 and 16), but, although to a lesser extent, also at the N-terminus.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Liskamp, Professor Robert
Authors: de Jong, R., Rijkers, D.T.S., and Liskamp, R.M.J.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Helvetica Chimica Acta
ISSN:0018-019X
ISSN (Online):1522-2675

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