stRRL

Antimicrobial Peptide

stRRL is a 7–amino acid hydrocarbon‑stapled amphiphilic peptide engineered to enhance structural stability and antimicrobial potency. The hydrocarbon staple enforces a helical conformation, improving resistance to proteolytic degradation and preserving activity in high-salt environments. Despite its ultrashort length, stRRL maintains strong membrane‑disruptive effects against microbial pathogens, making it a compact and robust model for next‑generation antimicrobial design.

Diseases Target

stRRL is designed to act against antibiotic-resistant bacteria that remain hard to treat under physiological (high-salt, serum-rich) conditions. Its short, stapled helical structure enables potent antimicrobial activity and structural stability, making it a promising template for next‑generation anti‑superbug therapeutics.

Stapling Strategy

Fmoc-(S)-2-(4-pentenyl)alanine (Fmoc-(S5)-OH, CAS: 288617-73-2) enables the solid-phase peptide synthesis (SPPS) of the ultrashort stRRL peptide. During assembly, Fmoc-(S5)-OH is incorporated at i,i+4 positions within the RRR core sequence, followed by ruthenium-catalyzed ring-closing olefin metathesis to generate the (CH₂)₄ hydrocarbon staple.

Technical specification

	Sequency :	Ac-L(S5)RRL(S5)R-NH₂
	MW :	1004.27 g/mol
	Purity :	> 95%
	Counter-Ion :	TFA Salts
	Delivery format :	Lyophilized

Price

Product	Size	Price €	Price $
SB329-1mg	1 mg	478	573
SB329-5mg	5 mg	608	730
SB329-10mg	10 mg	827	992

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If your target is not listed, we offer custom stapled peptide design and synthesis. Whether you require sequence optimization, specific modifications, or larger production quantities, our team can support your project. Submit your project details and we will provide a personalized proposal.

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2023 Aug 24;66(16):11414-11427. doi: 10.1021/acs.jmedchem.3c00856. Epub 2023 Aug 2.

Ultrashort All-Hydrocarbon Stapled α-Helix Amphiphile as a Potent and Stable Antimicrobial Compound

Abstract

The ravaging effect of drug-resistant bacteria has heightened the need for the development of membrane-soluble antimicrobial peptides (AMPs). However, their potential for clinical use is hindered by issues such as poor biocompatibility, salt sensitivity, and proteolytic lability. In this study, a series of ultrashort stapled cyclization heptapeptides were obtained by inserting all-hydrocarbon staples. StRRL with the highest therapeutic index (TI = 36.3) was selected after evaluating its antibacterial and toxic activity. Furthermore, stRRL demonstrated exceptional performance in high-protease and high-salt environments, making it an effective weapon against bacteria like Escherichia coli in a mouse peritonitis-sepsis model. The membrane lytic mechanism of stRRL, which operates from outside to inside, gives it a low drug-resistant tendency. This suggests that stRRL has the potential to replace antibiotics as a powerful candidate in tackling bacterial infection. In conclusion, the ultrashort all-hydrocarbon stapled antimicrobial amphiphiles inaugurated a novel entrance to the advancements of highly stable peptide compounds.

2023 Sep 2;12(9):1400. doi: 10.3390/antibiotics12091400

Peptide Stapling Applied to Antimicrobial Peptides

Abstract

Antimicrobial peptides (AMPs) are considered a promising therapeutic approach against multi-drug resistant microorganisms. Besides their advantages, there are limitations to be overcome so that these molecules can become market competitive. One of the biggest limitations is proteolytic susceptibility, which could be overcome by structural modifications such as cyclization, especially for helix-constraining strategies. Over the years, many helix stabilization techniques have arisen, such as lactam-bridging, triazole-based, N-alkylation and all-hydrocarbon stapling. All-hydrocarbon stapling takes advantage of modified amino acid residues and olefinic cross-linking to constrain peptide helices. Despite being a well-established strategy and presenting efficient stability results, there are different limitations especially related to toxicity. In this review, recent studies on stapled AMPs for antimicrobial usage are explored with the aim of understanding the future of these molecules as putative antimicrobial agents.

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