Peptides and Peptidomimetics

At CellMosaic, we offer custom synthesis of natural peptides, as well as modified peptides such as peptidomimetics, peptides with orthogonal functional groups, fully protected peptides, chimeric peptides, fluorescent or biotin-labeled peptides, peptide–oligo conjugates, and peptide-antibody/protein/enzyme conjugates. We use peptide synthesizer for milligram to gram scale synthesis. In order to obtain the highest quality, all of our peptides are synthesized using the most efficient HATU or HCTU coupling reagent, in contrast to the less efficient HBTU generally used by other peptide houses to reduce costs. We use an Fmoc peptide protocol with modifications deemed necessary to make the highest quality racemization-free peptide.

At CellMosaic, we carry some peptides and modified peptides, please click here to check some of our products.

We also carry Personalized Conjugation Kits (PerKit™) for peptide labeling and conjugation, please click here to check our PerKit™ product line.

For large scale or project beyond the scope of PerKit™ configuration, please contact us for a quote.   


Cys-Containing Peptide 

Cysteine has a free thiol group that can be specifically modified or conjugated with other molecules through well-established thiol chemistry; for example, by reacting with another thiol compound to form a cleavable disulfide bonded conjugate, or by reacting with a maleimide or an alkyl halide compound to form a stable thiol ether-bonded conjugate. N-terminal Cys-containing peptides have been used frequently for coupling with an immunogen carrier, such as KLH or BSA, for immunization purposes. Racemization of Cys residues is known to occur during standard HBTU and HATU coupling. This racemization can lead up to 40% byproduct and, in many cases, the racemized products are difficult to purify using standard reverse phase HPLC. To minimize the racemization of Cys residues (and histidine residues) during peptide synthesis, we intervene and perform manual couplings for all Cys and His residues. The outcome of such processes is high quality Cys or His-containing peptides. For peptides containing several Cys residues, we can selectively protect and deprotect Cys for labeling and conjugation. We can also selectively manage inter- or intramolecular disulfide bonds using orthogonal protecting groups for Cys.

Below is an example of a Cys-containing peptide synthesized using the standard automatic procedure (left) vs. manual intervention and special coupling (right)

.Cys peptide1cys peptide2

 


Aminooxy Peptide 

Aminooxy (-ONH2) is known to react quantitatively with ketone or aldehyde-containing compounds under very mild near physiological conditions. The resulting oxime compound is stable for most biological applications. The oxime bond can be further reduced to a more stable imine bond. Despite their usefulness, aminooxy peptides are not easy to make. Commercially available Fmoc protected aminooxy amino acid analogs suffer from double acylation during peptide synthesis. However, using the di-Boc protected aminooxy amino acid results in very poor yield of peptide during TFA cleavage because of acidic decomposition. At CellMosaic, we address this issue by synthesizing a special aminooxy monomer for peptide synthesis and using a clean cleavage cocktail. 

aminooxy peptide

 


Keto Peptide

Keto peptides have frequently been synthesized at CellMosaic. Keto peptides can react with any aminooxy or hydrazine-containing compound.

 ketopeptide

 


C-Terminal Acid Modification

Peptides can be selectively labeled or conjugated through the C-terminal carboxylic acid. To perform such a conjugation for peptides containing few internal Asp and Glu residues and other functional groups, such as free amine and thiol, the peptide needs to be fully protected during modification and conjugation. Usually, trityl chloride or Rink acid resin can be used for synthesizing such fully protected peptide acids. The fully protected peptide acid can then react with any molecule of interest in solution. 

fullyprotected


Selected Examples:

  • Peptide Labeling Example 1: Biotinylation of a peptide (>99.9% purity by HPLC for a single labeled product)

    Peptide Labeling

    Peptides can be labeled using a variety of methods depending on their amino acid composition. The N-terminal amine can be labeled if no internal Lys residues are present in the peptide. The C-terminal acid can be labeled if no Glu and Asp residues are...

  • Peptide—Oligo Conjugate Example 1: Synthesis and purification of BHQ2 oligo-peptide conjugates.

    Peptide—Oligo Conjugate

    At CellMosaic, we routinely synthesize oligo-peptide conjugates for customers, in particularly, the ones that customers have difficulties in obtaining themselves due to the properties of the starting oligos or peptides. We use various strategies to...