Nucleic Acid Related Compounds. 127. Selective N-Deacylation of N,O-Peracylated Nucleosides in Superheated Methanol¹

Abstract

[reaction: see text] Solutions of peracylated adenosine, cytidine, and related nucleoside derivatives undergo selective N-deacylation upon heating at elevated temperatures (oil bath > or = 105 degrees C) in methanol. An increase in the bulk of the N-acyl group has little effect on the rate of N-deacylation but increases the N/O selectivity ratio. Extended heating is required for N-deacylation with arylcarboxylic acid derivatives. Contamination with acidic or basic reagent residues is avoided.

Synthesis of Purine and 7‐Deazapurine Nucleoside Analogues of 6‐N‐(4‐Nitrobenzyl)adenosine; Inhibition of Nucleoside Transport and Proliferation of Cancer Cells

“…Volatiles were evaporated in vacuo and the residue was column chromatographed (EtOAc) to give 2′,3′,5′-tri- O -acetyltubercidin ( 3 ; 337 mg, 86%) as a colorless foam with data as reported. [33] …”

Supramolecular synthons and pattern recognition in adenine amides – synthesis, structures and thermal properties

“…H-bonding of the amide linkage plays an important role in the association process of molecules, which is used in gel stabilisation (12). In addition, the incorporation of the amide group by way of an amidation process is a useful and widely applied methodology for the protection of amines in organic synthesis (13). The strong tendency of amides to form hydrogen bonds, as well as their donor-acceptor properties, are the main factors responsible for the stabilisation of the secondary structure of proteins (14,15) and the formation of their supramolecular complexes with nucleic acids (16).…”

“…, 4.08 (t, J ¼ 6.5 Hz, 2H, ZOC(18) H 2 Z) 7.08 (dd, J ¼ 8.9 Hz, 2H, C(16,14) H), 8.11 (dd, J ¼ 8.9 Hz, 2H, C(17,13) H), 8.48 (s, 1H, C (8) H), 8.72 (s, 1H, C (2) H), 11.34 (br s, 1H, N (10) H), 12.34 (br s, 1H, N (7) H). 13 C NMR (600 MHz, DMSO-d 6 ) d ¼ 14.1 (ZCH 3 ), 22.7 (ZCH 2 Z), 26.0 (ZCH 2 Z), 29.1 (ZCH 2 Z), 29.3 (ZCH 2 Z), 29.6 (ZCH 2 Z), 29.6 (ZCH 2 Z), 29.6 (ZCH 2 Z), 29.7 (ZCH 2 Z), 31.9 (ZCH 2 Z), 68.6 (ZOCH 2 Z), 114.9 (C ar ), 123.7 (C ar ), 129.8 (C ar ), 143.5 (C ade ), 144.1 (C ade ), 152.4 (C ade ), 162.5 (ZOC ar ), 163.6 (C ade ), 165.7 (NCO).…”

A Route to Water‐Soluble Molecularly Templated Nanoparticles Using Click Chemistry and Alkyne‐Functionalized Hyperbranched Polyglycerol

“…Its nucleobase, adenine, is known to function as a signaling molecule in G protein coupled receptors 11 and adenine‐based templates have already been investigated for the production of molecularly imprinted polymers 7a,12 . Chemically, adenosine is known to form up to five ester/amide bonds when treated with acid chlorides, 13 allowing the synthesis of a complex core for polymer grafting and subsequent hydrolytic template removal. There are also a large number of related nucleosides and nucleobases available to test the binding selectivity of such a mMIP.…”