Links

Tools

Export citation

Search in Google Scholar

Synthesis of Trishomocubane Amino Acid Derivatives

Journal article published in 2015 by T. Govender ORCID, Hk K. Hariprakasha, Hg G. Kruger, T. Raasch
This paper was not found in any repository; the policy of its publisher is unknown or unclear.
This paper was not found in any repository; the policy of its publisher is unknown or unclear.

Full text: Unavailable

Question mark in circle
Preprint: policy unknown
Question mark in circle
Postprint: policy unknown
Question mark in circle
Published version: policy unknown

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.