5-Amino-5-deoxyshikimic Acid as a Versatile γ-Amino Acid for Peptidomimetic Synthesis

Suć Sajko, Josipa; Pahović, Franko; Jerić, Ivanka (2026) 5-Amino-5-deoxyshikimic Acid as a Versatile γ-Amino Acid for Peptidomimetic Synthesis. ACS Omega, 11 (9). pp. 15559-15565. ISSN 2470-1343

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Abstract

An efficient and scalable four-step synthesis of the 5-amino-5-deoxyshikimic acid derivative is described. This cyclic, unsaturated γ-amino acid was employed in both solution- and solid-phase peptide syntheses to afford products of high purity and yield. Furthermore, functionalization of the secondary hydroxyl groups was demonstrated, enabling systematic structural diversification and optimization of aminocarbasugar derivatives for potential applications in foldamer design, catalysis, and drug discovery.

Item Type:	Article
Uncontrolled Keywords:	carbasugars; gamma amino acids; peptidomimetics
Subjects:	NATURAL SCIENCES > Chemistry > Organic Chemistry
Divisions:	Division of Organic Chemistry and Biochemistry
Projects:	Project title Project leader Project code Project type Neproteinogene aminokiseline za povećanje konformacijske raznolikosti peptida Ivanka Jerić IP-2022-10-9617 HRZZ
Depositing User:	Ivanka Jerić
Date Deposited:	18 Mar 2026 12:24
URI:	http://fulir.irb.hr/id/eprint/11365
DOI:	10.1021/acsomega.6c00988

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