A novel reagent, dialkylphosphite, for peptide synthesis.
The same dialkylphosphite reagent can be used for both N protection and C activation of amino acids. Two N-diisopropyloxyphosphinyl (Dipp) tripeptide esters were prepared, and nine N-Dipp-dipeptide acids were synthesized through the activated amide intermediate. The positive ion FAB-MS of N-Dipp-tripeptide showed novel cleavage patterns in that only the N-phosphoryl fragment ions gave intense peaks while the C-terminal series ions did not appear. This novel character might be useful for peptide sequence analysis. In addition, dialkyloxyphosphinyl group can be examined by 31P-NMR for peptide conformational analysis and inspection for the degree of racemization during the coupling reaction.
Zhao
Y F
YF
Department of Chemistry, Tsinghua University, Beijing, China.
Zhang
D Q
DQ
Xue
C B
CB
D000595:Amino Acid Sequence; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008969:Molecular Sequence Data; D010455:Peptides / Q000138:chemical synthesis*; D010757:Phosphorous Acids; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013844:Thiazoles; D053778:Thiazolidines
D010455:Peptides; D010757:Phosphorous Acids; D013844:Thiazoles; D053778:Thiazolidines; C033089:thiazoline-2-thione