Verdine and co-workers⁽¹⁾ described the use of Fmoc-pyrrolidine CE-Phosphoramidite to install (2R,3S)-2-hydroxymethyl-3-hydroxypyrrolidine (3-hydroxyprolinol) residues into DNA. Such oligonucleotides were found to be potent and selective inhibitors of E. coli 3-methyladenine DNA glycosylase II (AlkA). The pyrrolidine ring, which should be protonated under experimental conditions, is proposed to mimic the charged intermediate encountered during glycosyl hydrolysis. Related 3-hydroxyprolinol-bearing oligonucleotides have been made and subjected to hybridization studies.⁽²⁾

Ref:

1. Scharer, O. D.; Ortholand, J.-Y.; Ganesan, A.; Ezaz-Nikpay, K.; Verdine, G. L. J. Am. Chem. Soc. 1995, 117, 6623-6624.
2. Ceulemans, G.; Van Aerschot, A.; Rozenski, J. Herdewijn, P. Tetrahedron 1997, 53, 14957-14974.