Hydrogen-bonded DeUG x DAN heterocomplex: structure and stability and a scalable synthesis of DeUG with reactive functionality.
A convenient, scalable synthesis of the supramolecular building block 7-deazaguanine-based urea (DeUG) is reported. Incorporation of reactive moieties (DeUG azide 10 and alkyne 11 for copper-catalyzed azide-alkyne cycloadditions, "click chemistry") and a demonstration of transesterification (DeUG glycol, 12) highlights the versatility. X-ray structures of DeUG and a DeUG x DAN heterocomplex were obtained. K(assoc) for the 1.2 heterocomplex was estimated to be 2 x 10(8) M(-1) in chloroform.
Kuykendall
Darrell W
DW
Department of Chemistry, 600 South Mathews Avenue, University of Illinois, Urbana, Illinois 61801, USA.
Anderson
Cyrus A
CA
Zimmerman
Steven C
SC
D018360:Crystallography, X-Ray; D006147:Guanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D006860:Hydrogen Bonding; D008958:Models, Molecular; D015394:Molecular Structure; D009287:Naphthyridines / Q000737:chemistry*; D014508:Urea / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
C516002:2,7-diamido-1,8-naphthyridine; D009287:Naphthyridines; C516001:ureido-7-deazaguanine; D006147:Guanine; D014508:Urea