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Based on existing methods in cysteine chemistry a new strategy is described for repeating regioselective interstrand disulfide bridging of multiple cysteine peptides into heteromeric constructs crosslinked by a ladder of disulfides. The efficacy of this new approach is demonstrated by the successful assembly of three different collagenous peptides into heterotrimers in the defined α1/α2/α1' order.
α,β-Dehydrotryptophan 4 is synthesized by a sequence of reactions starting with the corresponding serine derivative 1. This procedure includes substitution reaction between indole and the methylamino group of the β-(N-methylamino)dehydroalanine derivative 3 in acetic acid. The key intermediate 3 is obtained by oxidation of 1 with dimethylsulfoxide activated by p-toluenesulfonyl chloride, followed...
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