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
Fmoc Glycine 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-allyl-glycine
C20H19NO4

NEW


CAS# 170642-28-1
(Cat# 65503)

(R)-N-Fmoc-allyl-glycine

CAS# 146549-21-5
(Cat# 65502)

(S)-N-Fmoc-allyl-glycine

N-Fmoc-2-(3'-butenyl)glycine
C21H21NO4

NEW

CAS# 865352-21-2
(Cat# 65505)

(R)-N-Fmoc-2-(3'-butenyl)glycine

CAS#851909-08-5
(Cat# 65504)

(S)-N-Fmoc-2-(3'-butenyl)glycine

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

NEW

CAS# 1093645-21-6
(Cat# 65507)

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

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

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

N-Fmoc-2-(5'-hexenyl)glycine
C23H25NO4

NEW

CAS# 1208226-88-3
(Cat# 65509)

(R)-N-Fmoc-2-(5'-hexenyl)glycine

CAS# 1251904-51-4
(Cat# 65508)

(S)-N-Fmoc-2-(5'-hexenyl)glycine

N-Fmoc-2-(6'-heptenyl)glycine
C24H27NO4

NEW

CAS# 1262886-63-4
(Cat# 65511)

(R)-N-Fmoc-2-(6'-heptenyl)glycine

CAS# 1058705-57-9
(Cat# 65510)

(S)-N-Fmoc-2-(6'-heptenyl)glycine

N-Fmoc-2-(7'-octenyl)glycine
C25H29NO4

NEW

CAS# 1191429-20-5
(Cat# 65513)

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

CAS# 1262886-64-5
(Cat# 65512)

(S)-N-Fmoc-2-(7'-octenyl)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-(2'-propenyl) alanine
C21H21NO4


CAS# 288617-76-5
(Cat# 64171)

(R)-N-Fmoc-2-(2'-propenyl) alanine

CAS# 288617-71-0
(Cat# 64170)

(S)-N-Fmoc-2-(2'-propenyl) alanine

N-Fmoc-2-(3'-butenyl)alanine
C22H23NO4

NEW

CAS# 1311933-82-0
(Cat# 65497)

 	(R)-N-Fmoc-2-(3'-butenyl)alanine

CAS# 288617-72-1
(Cat# 65496)

(S)-N-Fmoc-2-(3'-butenyl)alanine

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

CAS# 288617-77-6
(Cat# 64173)

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

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

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

N-Fmoc-2-(5'-hexenyl)alanine
C24H27NO4

NEW

CAS# 288617-78-7
(Cat# 65499)

(R)-N-Fmoc-2-(5'-hexenyl)alanine

CAS# 288617-74-3
(Cat# 65498)

(S)-N-Fmoc-2-(5'-hexenyl)alanine

N-Fmoc-2-(6'-heptenyl)alanine
C25H29NO4

NEW

CAS# 1311933-84-2
(Cat# 65501)

(R)-N-Fmoc-2-(6'-heptenyl)alanine

CAS# 1311933-83-1
(Cat# 65500)

(S)-N-Fmoc-2-(6'-heptenyl)alanine

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

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

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

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

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




Other Fmoc Amino Acids for Stapled Peptide Synthesis

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

Other Stapled Peptide Fmoc Amino Acids Chemical Structure

Fmoc-2,2-Bis(4'-pentenyl) glycine (B5)
2-(((9H-Fluoren-9-yl) methoxy) carbonylamino)-2-(pent-4-enyl)hept-6- enoic acid (B5)
C27H31NO4


CAS# 288617-76-5
(Cat# 64177)

Fmoc-2,2-Bis(4'-pentenyl) glycine (B5)

N-Fmoc-2-amino-2-(2-propenyl)-4-Pentenoic acid
C23H23NO4

NEW

CAS# 1311992-97-8
(Cat# 65514)

N-Fmoc-2-amino-2-(2-propenyl)-4-Pentenoic acid

N-Fmoc-2-amino-2-(3-butenyl)hex-5-enoic acid
C25H27NO4

NEW

CAS# 1311992-98-9
(Cat# 65515)

N-Fmoc-2-amino-2-(3-butenyl)hex-5-enoic acid

N-Fmoc-2-amino-2-(pent-4-enyl)dec-9-enoic acid
C30H37NO4

NEW

CAS# 1211504-14-1
(Cat# 65516)

N-Fmoc-2-amino-2-(pent-4-enyl)dec-9-enoic acid

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).