Prenylated Peptide Synthesis

The isoprene portion of the isoprenyl peptide plays an important role in the reversible binding of the peptide to the cell membrane and the regulation of peptide-protein interactions. Thanks to decades of experience in peptide modification and synthesis, CD Formulation can provide customers with peptide prenylation services according to different needs. Our common services include the design, synthesis, and purification of isoprenyl peptides.

The Importance of Peptide Prenylation Modification

Peptide prenylation is a common post-translational modification of peptides, also known as isoprenylation. This modification adds a farnesyl (C15) or geranylgeranyl (C20) isoprenoid moiety to a cysteine ​residue near the carboxyl terminus of the peptide, which commonly occurs at the C-terminus of about 2% of mammalian proteins. Prenylation is an important process that mediates protein-protein interactions and protein-membrane interactions. Peptides modified with prenylation play a crucial role in signal transduction. In addition, these prenylated peptides have inherent cell-penetrating ability.

Fig. 1 C-terminal prenylation. (Wang YC, et al., 2012)

Explore Our Custom Prenylated Peptide Synthesis Services

As experts in peptide modification, CD Formulation provides unparalleled peptide prenylation services to clients around the world. We have reliable synthesis procedures and superior peptide analysis technologies to solve any possible challenges in developing and producing peptide therapeutics.

Our team of peptide experts can perform the following procedures including but not limited to:

• Prenylated peptide design.
• Prenylated peptide synthesis.
• Prenylated peptides characterization.
• Prenylated peptide purification.
• Prenylated peptide process development.
• Prenylated peptide large-scale production.

Available Synthetic Strategies for Prenylated Peptide

Consider that the prenylation of peptides requires the addition of a lipid chain formed of three farnesyls or four geranylgeranyl isoprene units to a free thiol group. The synthesis of peptides containing farnesyl or geranylgeranyl groups is severely hampered by the significant acid lability of these groups, especially the all-trans configuration of the double bonds in the farnesyl and geranylgeranyl chains.

CD Formulation has developed a mature and reliable procedure for the synthesis of prenylated peptides. This procedure focuses on overcoming the acid instability of farnesyl and geranylgeranyl groups and improving the efficiency and purity of the products by optimizing reaction conditions and synthetic strategies.

• Protecting Groups: During the synthesis, we use protecting groups, such as tert-butyl protecting groups, to protect the free thiol groups to improve their stability in acidic environments.
• Optimizing Reaction Conditions: Adjusting pH, temperature, and reaction time for each reaction step to reduce the adverse effects of acidity on farnesyl and geranylgeranyl groups.
• Selecting a Suitable Solvent: Selecting a solvent that is not prone to interact with the peptide reduces side reactions in the reaction and ensures the selectivity of the product.
• Meticulous Step-by-Step Synthesis: A meticulous step-by-step synthesis strategy is used to gradually add isoprene units and purify them at each step to improve the purity of the final product.
• Post-Processing Steps: After the synthesis is completed, effective purification and post-processing steps, such as high-performance liquid chromatography HPLC, are taken to remove byproducts and unreacted reagents.

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:

Publication

CD Formulation has extensive experience with each prenylation 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 prenylation into your peptides. We look forward to cooperating with you.

How It Works

STEP 1

Submit a service request describing your specific research or development need.

STEP 2

We'll email you to provide your quote and confirm order details if applicable.

STEP 3

Execute the project with real-time communication, and deliver the final report promptly.