Synthesis and coupling reactions of alpha,alpha-dialkylated amino acids with nucleobase side chains.
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.
Azumaya
I
I
Department of Chemistry, Massachusetts Institute of Technology, Cambridge 02139, USA.
Aebi
R
R
Kubik
S
S
Rebek
J
J
D000225:Adenine / Q000737:chemistry*; D000478:Alkylation; D000596:Amino Acids / Q000737:chemistry*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D010081:Oxazolone; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013941:Thymine / Q000737:chemistry*
D000596:Amino Acids; D007202:Indicators and Reagents; D010081:Oxazolone; D000225:Adenine; D013941:Thymine