Abstract:
:A series of hydroxypyrroloindoline (Hpi) containing dipeptides along with the corresponding monomeric Hpi-α-amino acid (Hpi-2-carboxylate), were prepared by reacting a series of N α-protected-tryptophans in aqueous or biphasic [water/cyclopentyl methyl ether (CPME)] solutions containing Oxone® (potassium peroxymonosulfate) and acetone. This procedure avoids the tedious distillation of unstable dimethyldioxirane (DMDO), which is commonly used to oxidize indoles. Monomers N α-Boc-Hpi-OH and N α-Fmoc-Hpi-OH were readily incorporated by solid-phase peptide synthesis (SPPS) into a peptide containing a cysteine; in trifluoroacetic acid (TFA), the Hpi underwent intramolecular dehydrative condensation with the cysteine thiol to afford the anticipated tryptathionine crosslink. This eco- and user-friendly oxidative methodology greatly simplifies the synthesis of Hpi derivatives while enabling the synthesis of tryptathionine crosslinks characteristic of phalloidin and amanitin, two potent peptide toxins of present interest.
journal_name
Amino Acidsjournal_title
Amino acidsauthors
Blanc A,Xia F,Todorovic M,Perrin DMdoi
10.1007/s00726-016-2364-3subject
Has Abstractpub_date
2017-02-01 00:00:00pages
407-414issue
2eissn
0939-4451issn
1438-2199pii
10.1007/s00726-016-2364-3journal_volume
49pub_type
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