A novel [60]fullerene amino acid for use in solid-phase peptide synthesis

F Pellarini; D Pantarotto; T Da Ros; A Giangaspero; A Tossi; M Prato

doi:10.1021/ol015934m

A novel [60]fullerene amino acid for use in solid-phase peptide synthesis

Org Lett. 2001 Jun 14;3(12):1845-8. doi: 10.1021/ol015934m.

Authors

F Pellarini¹, D Pantarotto, T Da Ros, A Giangaspero, A Tossi, M Prato

Affiliation

¹ Dipartimento di Scienze Farmaceutiche, Università di Trieste, Piazzale Europa, 1, 34127 Trieste, Italy, and Dipartimento di Biochimica, Biofisica e Chimica delle Macromolecole, Università di Trieste, Via Giorgieri 1, 34127 Trieste, Italy.

PMID: 11405726
DOI: 10.1021/ol015934m

Abstract

[see structure]. A fullerene derivative containing a free amino group has been condensed with N-Fmoc-L-glutamic acid alpha-tert-butyl ester to give a C60-functionalized amino acid. The carboxylic end of this amino acid has been deprotected in acidic conditions, and the resulting acid has been used for solid-phase peptide synthesis. The final peptide, cleaved from the resin, was very soluble in water solutions and showed antimicrobial activity against two representative bacteria.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amino Acids / chemistry*
Anti-Bacterial Agents / chemical synthesis
Anti-Bacterial Agents / pharmacology
Carbon / chemistry*
Escherichia coli / drug effects
Fullerenes*
Microbial Sensitivity Tests
Peptides / chemical synthesis*
Peptides / pharmacology
Spectrometry, Mass, Electrospray Ionization
Staphylococcus aureus / drug effects

Substances

Amino Acids
Anti-Bacterial Agents
Fullerenes
Peptides
Carbon
fullerene C60