The innovative technique of hydrocarbon stapling in peptides
is introducing valuable new functionality to peptide-related research. AnaSpec is pleased to offer custom synthesis for hydrocarbon-stapled
peptides are peptides capable of forming stable alpha helical structure as
a result of “hydrocarbon stapling.”1,2 Many biological pathways, such as signal transduction, occur because of intracellular
protein-protein interactions, which frequently are mediated by the a-helix structures of proteins; however, the use of short protein fragments (peptides)
leads to a loss of secondary structure, such as alpha helical structure.
Short peptides are easily degraded by proteolysis and have difficulty in intact
cells penetration.1 Verdine’s group has shown that these problems could be overcome by a chemical
modification of an alpha-helical peptide they termed hydrocarbon-stapled peptide.1,2
The modified hydrocarbon-stapled peptide is helical, relatively
protease resistant, cell-permeable and binds with increased binding affinity
to its target. Hydrocarbon stapling may provide a useful strategy in researching
experimental and therapeutic modulation of protein-protein interactions as
well as in in vivo pharmacokinetics studies.
Figure 1. Strategy for hydrocarbon-stapled peptide with enhanced
To view a pre-print paper from the Journal of Molecular Biology entitled
“A Cell-penetrating Helical Peptide as a Potential HIV-1 Inhibitor,” reported by scientists from the Lindsley F. Kimball Research
Institute of the New York Blood Center, New York Structural Biology, AnaSpec,
Inc. and the National Cancer Institute-Frederick, please click here.
a poster on hydrocarbon-stapled peptides last year at the 20th
American Peptide Society. Click here to
download the PDF
Custom synthesis of unusual
peptides – glycopeptides, dye labeled peptides, FRET peptides, peptide
libraries, peptides with multiple disulfide bonds and heavy-isotope labeled
– The world's largest provider of new catalog peptides
- Walensky, LD. et al. Science
305, 1466 (2004).
- Schafmeister, CE. et al. J.
Am. Chem. Soc. 122, 5891 (2002).
- Qiu, W. et al. Tetrahedron
56, 2577 (2000).
- Belokon, Y. N. et al. Tetrahedron:
Asymmetry 9, 4249 (1998).