Peptide Ribonucleic Acids (PRNA). 2. A Novel Strategy for Active Control of DNA Recognition through Borate Ester Formation

Autor:	Narutoshi Minamimoto, and Yoshiaki Inaki, Yoshihisa Inoue, Takehiko Wada
Rok vydání:	2000
Předmět:	chemistry.chemical_classification Borax Stereochemistry chemistry.chemical_element Peptide General Chemistry Ribonucleoside Biochemistry Catalysis Nucleobase Boric acid chemistry.chemical_compound Colloid and Surface Chemistry chemistry Nucleic acid Moiety Boron
Zdroj:	Journal of the American Chemical Society. 122:6900-6910
ISSN:	1520-5126 0002-7863
DOI:	10.1021/ja9935456
Popis:	The effect of adding borax and boric acids on the nucleobase orientation and recognition behavior of novel mono- and oligomeric peptide ribonucleic acids (PRNAs) has been investigated. The base orientation of 5‘-amino-5‘-deoxyuridine and 5‘-amino-5‘-deoxycytidine was shown by CD and NOE difference spectral studies to switch from anti to syn in borate buffer or upon addition of borax. The origin of this phenomenon is elucidated to be the cooperative effect of the cyclic borate esterification of the sugar's cis-2‘,3‘-diol and the hydrogen-bonding interaction between the sugar's 5‘-amino proton and the base's 2-carbonyl oxygen. Because this new strategy for switching the base orientation through the addition of borate is potentially applicable to the recognition control of nucleic acids if the sugar's 5‘-proton and cis-2‘,3‘-diol remain unmodified, we synthesized a series of PRNAs, in which the 5‘-amino-5‘-deoxypyrimidine ribonucleoside moiety was appended to a mono- or oligo(γ-l-glutamic acid) backbone thro...
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::1070d6831e42246c530670cc10035705 https://doi.org/10.1021/ja9935456 Zobrazit plný text záznamu