Open AccessSynthesis and coupling reactions of alpha,alpha-dialkylated amino acids with nucleobase side chains.
Author(s) -
Isao Azumaya,
R. Aebi,
Stefan Kubik,
Julius Rebek
Publication year - 1995
Publication title -
proceedings of the national academy of sciences of the united states of america
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.011
H-Index - 771
eISSN - 1091-6490
pISSN - 0027-8424
DOI - 10.1073/pnas.92.26.12013
Subject(s) - side chain , chemistry , amino acid , nucleobase , tripeptide , thymine , steric effects , pyrimidine , stereochemistry , alpha (finance) , purine , organic chemistry , biochemistry , dna , polymer , medicine , construct validity , nursing , patient satisfaction , enzyme
Several di- and tripeptides containing protected purine (adenine) and pyrimidine (thymine) residues on their side chains were synthesized. The parent amino acids alpha, alpha-dialkylated in a symmetrical manner. An effective coupling procedure was developed for these sterically hindered amino acids: the fluoren-9-ylmethyloxycarbonyl-protected amino acid was dehydrated to its oxazolinone form, which was coupled in good yields with amino esters in hot tetrachloroethane.