J.H. van Maarseveen
- Fine-tuning the balance between peptide thioester cyclization and racemization
- European Journal of Organic Chemistry
- Volume | Issue number
- 2016 | 3
- Pages (from-to)
- Document type
- Faculty of Science (FNWI)
- Van 't Hoff Institute for Molecular Sciences (HIMS)
Ring-closure towards seven-membered bislactams containing an -amino acid and -alanine is problematic. Such difficult lactamizations are accompanied by side-reactions such as hydrolysis, oligomerization and racemization. By starting from linear peptide 4-methoxythiophenol esters, dilution to 1 mM in combination with phosphate buffer (pH 6.8) intermolecular reactions and racemization could be largely suppressed. Thioesters with the chiral residue at the C-terminus gave the bislactams in yields up to 60% and enantiomeric excess up to 99%. Enantiopure bislactams were obtained exclusively from the reversed sequence bearing -alanine at the C-terminus.
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