The incorporation of a single beta-aminoethane sulfonyl amide moiety in a highly amyloidogenic peptide sequence resulted in a complete loss of amyloid fibril formation. Instead, supramolecular folding morphologies were observed. Subsequent chemoselective N-alkylation of the sulfonamide resulted in amphiphilic peptide-based hydrogelators. It was found that variation of merely the alkyl chain induced a dramatic variation in aggregation motifs such as helical ribbons and tapes, ribbons progressing to closed tubes, twisted lamellar sheets and entangled/branched fibers.
Dedicated to Professor Dieter Seebach on the occasion of his 65th birthday Fmoc-protected b-aminoethane sulfonylchlorides can be employed for efficient automated solid phase synthesis of b-peptidosulfonamides and b-peptidosulfonamide/b-peptide hybrids containing one or more bpeptidosulfonamide residues. Thus, Fmoc-protected b-aminoethane sulfonylchlorides 5a ± c led to the hexa-bpeptidosulfonamide 9 and the nona-b-peptidosulfonamide 10. In addition, the b-peptidosulfonamide/b-peptide hybrids 13 and 16, consisting of six and nine b-residues, respectively, and containing a single b-peptidosulfonamide unit in the middle, as well as the peptidosulfonamide/b-peptide hybrid 15 with nine b-residues, including an N-terminal b-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 b-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.
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ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
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