Stapled Peptide Building Blocks

The innovative technique of hydrocarbon stapling in peptides is introducing valuable new functionality to peptide-related research. As demand grows for stapled peptides, peptide chemists will find AnaSpec a ready supplier for many of the stapled peptide building blocks (see Tables 1-3).

AnaSpec's world renowned custom peptide synthesis service also includes expertise and a wealth of experience in Hydrocarbon Peptide Stapling Synthesis. Email us to get more information. To obtain a free price quotation, please click here.

FRETPeptide Figure 1. A hydrocarbon stapled peptide can be synthesized using solid phase peptide synthesis. Two α-methyl, α-alkenyl containing amino acids are first incorporated into a peptide, followed by ring closure, deprotection and cleavage of peptide from the solid support.1
Fmoc Glycine derivatives
Fmoc Alanine derivatives

Hydrocarbon-stapled peptides are peptides capable of forming stable alpha helical structure as a result of "hydrocarbon stapling."2,3 Many biological pathways occur because of intracellular protein-protein interactions, which frequently are mediated by the α-helix structures of proteins. However, the use of short protein fragments (peptides) leads to a loss of secondary structure, which makes them susceptible to proteolysis and impermeable across cell membrane.2

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.

AnaSpec presented a poster on hydrocarbon-stapled peptides at the 20th American Peptide Society, entitled "A Cell-penetrating Helical Peptide as a Potential HIV-1 Inhibitor."

Hydrocarbon stapling modification generally results in a peptide that is:

✓ Helical
✓ Relatively protease resistant
✓ Cell-permeable
✓ Binds with increased binding affinity to its target

Fmoc Glycine Derivatives

Available in 5 sizes (100 mg, 500 mg, 1 g, 5 g and 10 g). Click chemical structure to get more detailed information.

Chirality
R S

N-Fmoc-2-(4'-pentenyl)glycine
C22H23NO4

 

CAS# 856412-22-1
(Cat# AS-65506)

(S)-N-Fmoc-2-(4'-pentenyl)glycine




Fmoc Alanine Derivatives

Available in 5 sizes (100 mg, 500 mg, 1 g, 5 g and 10 g). Click chemical structure to get more detailed information.

Chirality
R S

N-Fmoc-2-(4'-pentenyl) alanine
C23H25NO4

 

 

CAS# 288617-73-2
(Cat# AS-64172)

(S)-N-Fmoc-2-(4'-pentenyl) alanine

N-Fmoc-2-(7'-octenyl)alanine
C26H31NO4

CAS# 945212-26-0
(Cat# AS-64175)

(R)-N-Fmoc-2-(7'-octenyl)alanine

CAS# 288617-75-4
(Cat# AS-64174)

(S)-N-Fmoc-2-(7'-octenyl)alanine

References:

1. Kim, Y-W. et al. Nature Protocols 6, 761 (2011).
2. Walensky, LD. et al. Science 305, 1466 (2004).
3. Schafmeister, CE. et al. J. Am. Chem. Soc. 122, 5891 (2000).