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3'-(α-L-Aminoacylamido)deoxyadenosines are ribosomal A-site binders and mimic the nascent peptide accepting 3'-terminus of aminoacyl transfer RNA. Their α-amino groups exhibit intrinsic basicities in bulk water that differ by up to 1.8 pK(a) units. Only the neutral form of these nucleophiles can be active during ribosomal peptidyl transfer catalysis.


Kollappillil S Krishnakumar, Benoît Y Michel, Nhat Quang Nguyen-Trung, Bernard Fenet, Peter Strazewski. Intrinsic pKa values of 3'-N-α-l-aminoacyl-3'-aminodeoxyadenosines determined by pH dependent 1H NMR in H2O. Chemical communications (Cambridge, England). 2011 Mar 21;47(11):3290-2

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PMID: 21286631

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