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Fatty Acid Modified Peptide Synthesis

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To improve the pharmacokinetics of peptides, conjugating peptides to lipids is a popular approach. It significantly prolongs the half-life in circulation. The most typical derivatization involves long-chain fatty acids. Fatty acid-conjugated peptides can also be used in many different applications, such as to increase their antimicrobial activity or eukaryotic cytotoxicity. CD Formulation excels at adding a variety of different lipid molecules to your peptide sequence to generate lipopeptides with unique properties.

What is Peptide Fatty Acid Esterification?

Peptide fatty acid esterification, commonly dubbed peptide lipidation, unfurls as a captivating yet complex biochemical voyage, wherein a fatty chain becomes entwined with a peptide molecule in a dance of molecular intricacy. This elaborate transformation transcends the simplistic notion of modification; it stands as a powerful tactic to enhance and fine-tune the properties of peptide and protein-centric therapeutics. By embedding lipid moieties into peptides, researchers unlock a myriad of possibilities, enhancing solubility, stability, and bioavailability in the ever-evolving landscape of drug development. Using lipidation for peptide drugs can notably increase the half-life and cell permeability of these molecules, enabling dosing every day, week, or longer. Presently, many lipidated peptide drugs have received FDA approval, including semaglutide, liraglutide, and tazeparatide.

Fig. 1 Synthesis of palmitoylated peptides. Fig. 1 Solid phase synthesis of palmitoylated peptides. (Hanna CC, et al., 2022)

Explore Our Custom Fatty Acid Modified Peptide Synthesis Services

Within the intriguing realm of peptide synthesis, our laboratory stands as a veritable hub of innovation, offering an array of methodologies for the intricate art of fatty acid conjugation. Here, the possibilities unfurl enabling us to seamlessly attach fatty acids to the N-terminus or to the side chains of lysine residues. Moreover, we delve into the unique modification of cysteine residues, skillfully transforming them into thioester derivatives through the adept integration of fatty acids.

Our comprehensive suite of services encompasses a plethora of approaches, ensuring that every project we undertake is imbued with precision and creativity.

Our services include but are not limited to:

Fatty acid-modified peptide design.
Fatty acid-modified peptide synthesis.
Fatty acid-modified peptide purification.

Fatty Acid Options At CD Formulation

Name	IUPAC Name	Structure
Palmitic Acid	Hexadecanoic Acid
Myristic Acid	Tetradecanoic Acid
Caprylic Acid	Octanoic Acid
Capric Acid	Decanoic Acid
Lauric Acid	Dodecanoic Acid
Stearic Acid	Octadecanoic Acid
Sebacic Acid	Decanedioic Acid
Suberic Acid	Octanedioic Acid
Oleic Acid	(9Z)-Octadec-9-Enoic Acid

Cholesterol Modified Peptide Synthesis

In addition to fatty acid conjugation, our scientists also apply cholesterol derivatization to improve the pharmacokinetics of peptides. Cholesterol can be conjugated to peptides via cysteine inserted at the N-terminus or the C-terminus.

Fig. 2 Cholesterol-peptide conjugates. Fig. 2 Synthesis of cholesterol-peptide conjugates. (Tang Q, et al., 2013)

Our Peptide Lipidation Technology

At CD Formulation, we use different lipid synthesis technologies to meet the various needs of specific lipopeptides. Our common lipid synthesis technologies include:

Solid Phase Peptide Synthesis (SPPS)

SPPS adds protected amino acids to a solid support sequentially, followed by deprotection and cleavage to release the peptide. Lipid compounds are attached to the peptide via DCC or EDC coupling agents.

Liquid Phase Peptide Synthesis (LPPS)

LPPS technology utilizes protected amino acids to react with lipid compounds in a liquid solution, followed by purification and deprotection to obtain the final lipopeptide.

Chemical Ligation

Our scientists synthesize the peptide and lipid components separately and then apply chemical ligation reactions to connect them together.

Combination Approach

Depending on the different needs of lipopeptides, our technical team will use a hybrid approach to complete the lipidation process. We have developed novel combination approaches to synthesize and purify hydrophobic peptide-modified lipopeptides.

Peptide Manufacturing & Analytical Services

In addition to peptide synthesis capabilities, CD Formulation combines flexible GMP manufacturing facilities with cutting-edge peptide analytical knowledge to provide a full range of quality control testing services to accelerate the commercialization of your products, including:

Peptide identification (ESI-MS).
Peptide Molecular weight determination.
Peptide sequencing.
Peptide quantification/peptide content determination.
Peptide purity and impurity analysis (HPLC/UV).
Amino acid sequence.
Amino acid composition determination.
Net peptide content.

Enantiomeric purity testing (GC/MS; LC).
Residual counterion testing (e.g. TFA).
Elemental analysis.
Residual solvent testing.
Water content testing (GC or KF).
Peptide solubility testing.
Peptide stability testing.

Optical rotation determination.
Bioburden testing(TAMC/TYMC).
Bacterial endotoxin testing.
Sterility testing.
Cytotoxicity testing.
Process/product related impurity testing.
Other pharmacopoeia testing.

Publication

Published Data

Technology: N-Terminal Fatty Acid Modification

Journal: Eur J Med Chem.

IF: 5.94

Published: 2019

Results:

The authors designed and synthesized a number of new anoplin analogs. Anoplin A is the smallest linear α-helical antimicrobial peptide. Their antimicrobial activity, safety, secondary conformation, biofilm inhibition activity, ability to induce resistance, and possible antimicrobial mechanisms were studied. The experimental results showed that the conjugation of fatty acids to the N-terminus of anoplin-D4,7 and dimerization using click chemistry can enhance the antimicrobial activity of the peptides, and this strategy is a promising strategy to obtain potent antimicrobial agents.

Fig. 3 Fatty acid modified-antimicrobial peptide. Fig. 3 Design and synthesis of new N-terminal fatty acid modified-antimicrobial peptide analogues. (Zhong C, et al., 2019)

CD Formulation has extensive experience with each fatty acid modification of peptides. Please don't hesitate to contact us if you are interested in our services, and to learn more about the possibilities of incorporating fatty acid groups into your peptides. We look forward to cooperating with you.

References

Hanna CC, Kriegesmann J, Dowman LJ, et al. Chemical Synthesis and Semisynthesis of Lipidated Proteins. Angew Chem Int Ed Engl. 2022 Apr 4;61(15):e202111266.
Kurtzhals P, Østergaard S, Nishimura E, et al . Derivatization with fatty acids in peptide and protein drug discovery. Nat Rev Drug Discov. 2023 Jan;22(1):59-80.
Tang Q, Cao B, Wu H, et al. Cholesterol-peptide hybrids to form liposome-like vesicles for gene delivery. PLoS One. 2013;8(1):e54460.
Zhong C, Liu T, Gou S, et al. Design and synthesis of new N-terminal fatty acid modified-antimicrobial peptide analogues with potent in vitro biological activity. Eur J Med Chem. 2019 Nov 15;182:111636.

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