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• W2172281454 startingPage "7697" @default.
• W2172281454 abstract "The Nα-Fmoc-peptide isocyanates 3a−q, 4a−c, and 5a−c were prepared by the Curtius rearrangement of Nα-Fmoc-peptide acid azides in toluene under thermal, microwave, and ultrasonic conditions. All the Nα-Fmoc-oligo-peptide isocyanates made were isolated as stable crystalline solids with 71 to 94% yield and were fully characterized by 1H NMR, 13C NMR, and mass spectroscopy. Their utility for the synthesis of oligo-α-peptidyl ureas 7a−f and 8a−c by the divergent coupling approach was demonstrated. The coupling of Nα-Fmoc-dipeptide isocyanates with amino acid ester or with N,O-bis(trimethylsilyl)amino acids resulted in Nα-Fmoc-tripeptidyl urea ester and acids containing one each of peptide bond and urea bond. The divergent approach is extended to the synthesis of tetrapeptidyl ureas by the 2 + 2 strategy using bis-TMS−peptide acid as an amino component. To incorporate urea bonds in adjacent positions, Nα-Fmoc-peptidyl urea isocyanates 9a−d were prepared and employed in the synthesis of three tetrapeptidyl ureas 10a−b and 11 containing one peptide bond and two urea bonds in series from the N-terminal end. The protocol was then employed for the synthesis of five urea analogues 13−15, 18, and 21 of [Leu5]enkephalin containing urea bonds at the 2, 3, 4 positions as well as at the 2, 4 and 2, 3, 4 positions. The analogue 2l was made by the convergent synthesis by the N → C terminal chain extension. Finally, two urea analogues 22 and 23 of repeat units of bioelasto polymers, namely Val-Pro-Gly-Val-Gly-OH and Pro-Gly-Val-Gly-Val-OH, were synthesized incorporating the urea bond by the concomitant isocyanate generation and urea bond formation under thermal conditions." @default.
• W2172281454 created "2016-06-24" @default.
• W2172281454 creator A5046992365 @default.
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• W2172281454 date "2006-08-29" @default.
• W2172281454 modified "2023-09-23" @default.
• W2172281454 title "Preparation, Isolation, and Characterization of <i>N</i>^α-Fmoc-peptide Isocyanates: Solution Synthesis of Oligo-α-peptidyl Ureas" @default.
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• W2172281454 doi "https://doi.org/10.1021/jo0611723" @default.
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