6533b826fe1ef96bd1283e2c

RESEARCH PRODUCT

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)

Paweł KafarskiBłażej DziukMaciej MakowskiBartosz ZarychtaPaweł Lenartowicz

subject

chemistry.chemical_classificationphosphonopeptidesdehydrodipeptidesDouble bond010405 organic chemistryElectrophilic additionOrganic Chemistry010402 general chemistry01 natural sciencesBiochemistryMedicinal chemistry0104 chemical sciencesInorganic Chemistrychemistry.chemical_compoundchemistryBromideMichael additionMichael reactiondehydrophosphonodipeptides

description

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.

https://dx.doi.org/10.6084/m9.figshare.5040271.v1