Article Sidebar
Published:
Sep 22, 2015Keywords:
Article Details
Copyright for articles published in this journal is retained by the journal.
SAJChem applies the Creative Commons Attribution (CC BY) license to manuscripts we publish. This license was developed to facilitate open access – namely, free immediate access to, and unrestricted reuse of, original works of all types. Under this license, authors agree to make articles legally available for reuse, without permission or fees, for virtually any purpose. Anyone may copy, distribute or reuse these articles, as long as the author and original source are properly cited.
Main Article Content
Synthesis of Trishomocubane Amino Acid Derivatives
Abstract
The synthesis of four novel trishomocubane amino acid derivatives is described. The hydantoin precursor and bis-Boc protected hydantoin (>95% yield) were previously reported. A mild hydrolysis of the bis-Boc hydantoin with lithium hydroxide at room temperature quantitatively yielded the corresponding novel cage amino acid. The cage amino acid was characterized as the Fmoc derivative. Although the Fmoc amino acid is partially deprotected after three weeks in a refrigerator, it is stable enough for use in Solid Phase Peptide Synthesis (SPPS). The Fmoc cage amino acid was converted to the acid fluoride with cyanuric fluoride. The acid fluoride is required for activation of the cage amino acid in SPPS. Esterification of the sterically hindered trishomocubane amino acid is also reported, indicating sufficient reactivity of the acid function for potential use in SPPS.
Keywords: Trishomocubane amino acid, hydantoin, Fmoc protection, t-Boc protection, acid fluoride, esterification.
