Scaling Azapeptide with N -Fmoc-Aza-Tripeptide from Resonant Acoustic Mixing of N -Fmoc-Amino Hydrazide and N -Succinimidyl Carbamate

Michael Quagliata; Justin Desjardins-michaud; Nassim Maarouf-Mesli; Ida Boccino; Zahra Bigdeli; Felix Polyak; William D. Lubell

doi:10.1021/acs.orglett.6c00458

Scaling Azapeptide with N -Fmoc-Aza-Tripeptide from Resonant Acoustic Mixing of N -Fmoc-Amino Hydrazide and N -Succinimidyl Carbamate

Organic Letters 2026

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Authors: Michael Quagliata, Justin Desjardins-michaud, Nassim Maarouf-Mesli, Ida Boccino, Zahra Bigdeli, Felix Polyak, William D. Lubell

DOI: 10.1021/acs.orglett.6c00458

Cited by: 2

References: 47

Abstract

Sustainable and scalable solution-phase synthesis of aza-tripeptide building-blocks was achieved by using resonant acoustic mixing (RAM). Hydrazinolysis gave N -(Fmoc)amino hydrazide without Fmoc cleavage, diacylation, epimerization, and chromatographic purification. N -(Suoc)amino esters and amides were made without hydantoin formation by using disuccinimidyl carbonate. Exceptional solubilizing properties of N -methylmorpholine and catalysis using 1-hydroxy-7-azabenzotriazole enabled RAM-assisted coupling of hydrazine and active carbamate components to afford aza-di-, -tri-, and -tetrapeptides. In solid-phase synthesis, aza-tripeptide coupled cleanly, giving access to biologically relevant azapeptides.

Fields of Study & Subjects

Chemical Synthesis and Analysis Supramolecular Self-Assembly in Materials Carbohydrate Chemistry and Synthesis

Publication details

Journal / source: Organic Letters
Publisher: American Chemical Society (ACS)
Volume: 28
Issue: 11
Pages: 3510–3516
Publication date: 5 March 2026
Language: EN

References 47