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- Title
Automated Solid-Phase Synthesis and Structural Investigation of β-Peptidosulfonamides and β-Peptidosulfonamide/ β-Peptide Hybrids: β-Peptidosulfonamide and β-Peptide Foldamers are Two of a Different Kind.
- Authors
de Jong, Remco; Rijkers, Dirk T. S.; Liskamp, Rob M. J.
- 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.
- Publication
Helvetica Chimica Acta, 2002, Vol 85, Issue 12, p4230
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.200290008