Homochiral oligomers with highly flexible backbones form stable H-bonded duplexes.

ABSTRACT: Two homochiral building blocks featuring a protected thiol, an alkene and a H-bond recognition unit (phenol or phosphine oxide) have been prepared. Iterative photochemical thiol-ene coupling reactions were used to synthesize oligomers containing 1-4 phosphine oxide and 1-4 phenol recognition sites. Length-complementary H-bond donor and H-bond acceptor oligomers were found to form stable duplexes in toluene. NMR titrations and thermal denaturation experiments show that the association constant and the enthalpy of duplex formation increase significantly for every additional H-bonding unit added to the chain. There is an order of magnitude increase in stability for each additional H-bonding interaction at room temperature indicating that all of the H-bonding sites are fully bound to their com

SUBMITTER: Nunez-Villanueva D 

PROVIDER: S-EPMC5308278 | biostudies-literature | 2017 Jan

REPOSITORIES: biostudies-literature