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Synthesis of a 7‐Deazaguanine‐Functionalized β‐Amino Acid: Improved Specificity of β‐Peptide Helix Organization
Author(s) -
Chakraborty Pradip,
Brückner Arndt M.,
Diederichsen Ulf
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200501003
Subject(s) - chemistry , nucleobase , guanine , peptide , helix (gastropod) , peptide nucleic acid , stereochemistry , triple helix , amino acid , combinatorial chemistry , selectivity , base pair , derivative (finance) , nucleic acid , dna , nucleotide , biochemistry , catalysis , ecology , biology , snail , financial economics , economics , gene
Nucleobase‐functionalized β‐peptides are a suitable scaffold for the construction of well‐defined tertiary structures organized by nucleobase pair recognition. Since guanine‐rich oligomers are especially known to form higher aggregates, an enantiomerically pure 7‐deazaguanine ( z G)‐functionalized nucleo‐β 3 ‐amino acid was synthesized from a β‐lactam derivative as a key intermediate. Incorporated into β‐peptide 14‐helices it was possible to reduce aggregation phenomena and to increase recognition selectivity. Evidence for base‐pair‐mediated helix recognition was obtained by temperature‐dependent UV and CD spectroscopy. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)