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Updated: Jun 12, 2026

Construction of Cyclic Cell-Penetrating Peptides for Enhanced Penetration of Biological Barriers
Published on: September 19, 2022
A simple quick route to fullerene amino acid derivatives
T Amanda Strom1, Andrew R Barron
1Richard E. Smalley Institute for Nanoscale Science and Technology, Center for Biological and Environmental Nanotechnology, and Department of Chemistry, Rice University, Houston, Texas 77005, USA.
Abstract:
Two new fullerene amino acids have been prepared by dipolar addition to C(60) of either the Boc- or Fmoc-Nalpha-protected azido amino acids derived from phenylalanine and lysine. UV-visible and CV studies indicate the as prepared amino acids are a mixture of 5,6-open (major product) and 6,6-closed (minor product) derivatives that may be readily separated.
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Structures of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...