Michael additions to double bonds of esters of N-protected (s)-phenylalanyldehydroalanine (X-(s)-Phe-ΔAla-OMe) and its phosphonic acid counterpart (X-(s)-Phe-ΔAla-PO(OEt)₂)

GRAPHICAL ABSTRACT

ABSTRACT

Electrophilic addition of amines, thiols and bromide to the double bonds of model dehydrodipeptides and dehydrophosphonodipeptide was studied. The double bond in these two classes of peptides reacted similarly and gave the same products. These results indicate that dehydropeptides are very good candidates as substrates for modifications of peptide side-chains.

KEYWORDS:

• Dehydrodipeptides
• dehydrophosphonodipeptides
• phosphonopeptides
• Michael addition

Funding

Support from the National Science Centre, Poland (Grant 2016/21/B/ST5/00115), is gratefully acknowledged.