52298-32-5Relevant articles and documents
On the electron withdrawing nature of ethers in glycosylation chemistry
Marqvorsen, Mikkel H.S.,Brink?, Anne,Jensen, Henrik H.
supporting information, (2019/12/24)
The present paper is a commentary on the electronic effects that protecting groups exert on glycosylation chemistry. Specifically, its purpose is to rectify the misguided use of the term electron donating benzyl groups, which hardly makes sense in the context of protecting groups on alcohols in saturated systems such as carbohydrates. It is argued that benzyl ethers (OBn) should rightfully be referred to as being inductively electron withdrawing, even if they are less so than benzoyl esters (OBz).
Inhibition of peptidylglycine α-amidating monooxygenase by exploitation of factors affecting the stability and ease of formation of glycyl radicals
Barratt, Brendon J. W.,Easton, Christopher J.,Henry, David J.,Li, Iris H. W.,Radom, Leo,Simpson, Jamie S.
, p. 13306 - 13311 (2007/10/03)
Peptidylglycine α-amidating monooxygenase catalyzes the biosynthesis of peptide hormones through radical cleavage of the C-terminal glycine residues of the corresponding prohormones. We have correlated ab initio calculations of radical stabilization energies and studies of free radical brominations with the extent of catalysis displayed by peptidylglycine α-amidating monooxygenase, to identify classes of inhibitors of the enzyme. In particular we find that, in closely related systems, the substitution of glycolate for glycine reduces the calculated radical stabilization energy by 34.7 kJ mol -1, decreases the rate of bromination with N-bromosuccinimide at reflux in carbon tetrachloride by a factor of at least 2000, and stops catalysis by the monooxygenase, while maintaining binding to the enzyme.
