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Isoacyl Dipeptides

Isoacyl dipeptides are used to prepare depsipeptides in which the peptide chain is attached to the side chain oxygen atom of serine or threonine residues instead of the alpha nitrogen atom.  Depsipeptides are less prone to aggregation than their standard peptide analogs because the structure of depsipeptides disrupts inter chain hydrogen bonding responsible for aggregation.  This also improves the solubility of depsipeptides compared to the standard analogs.  The depsipeptides are stable under acidic conditions and can be purified by HPLC.  When the pH is adjusted to 7.4 or greater, depsipeptides undergo O->N acyl shift to form the native peptide.  This provides an efficient way to prepare and purify difficult peptides in high yield.

Isoacyl dipeptides can be formed on solid phase resins, but acylating amino acid is subject to racemization.  When the reaction is performed in solution, however, the extent of racemization is negligible.  Therefore, preformed isoacyl dipeptides are utilized to incorporate the O-acyl unit.

Isoacyl dipeptides are useful building blocks for assembling large peptides and small proteins by segment condensation.  In addition to improving the solubility of peptides segments, isoacyl dipeptides have other benefits.  Unlike regular peptides, peptides containing an isoacyl dipeptide at the C-terminus can be coupled to other peptide segments with little racemization of the C-terminal amino acid.  By designing the peptide segments with isoacyl dipeptides at the C-terminals, large peptides or small proteins can be efficiently prepared in high diastereomeric purity.

AAPPTec offers the largest selection of high quality, high purity isoacyl dipeptides at very affordable prices. 

All isoacyl dipeptides are available in gram to kilogram quantities.  Please email AAPPTec at for a quotation on bulk quantities or use the On-Line Quote Request.