D Amino Acid Peptide Synthesis Service
* Please be kindly noted that our services can only be used for research to organizations or companies and not intended for individuals.
According to the central dogma established by classical naturalists and biologists, proteins/peptides were expected to be exclusively constituted by 20 building blocks, including 19 L-amino acids (L-AAs) and glycine, which is not chiral. At that time, special cases were reported for D-amino acids (D-AAs) containing proteins/peptides such as the presence of D-alanine in octopine derivatives from octopus.
From a functional point of view, these posttranslational and chemical modifications in D-AAs containing proteins/peptides confer on them an unusual stereochemistry mostly related to enhanced resistance to enzyme-catalyzed breakdown.
It is worth mentioning the composition of retro-inverso (RI) peptides, also known as all-D-retro peptides or retro-enantio peptides, which are composed of D-AAs assembled in the reverse order to that of their parent L-sequence.
Figure 1 Representation of the planar structure and chirality of hypothetic L-, diastereomeric, all-D- and RI-peptides, also highlighting their pros and cons.
Advantages of retro-inverso peptides:
- structural stability
- spatial orientation
- side-chain topology
- the peptide's bioactivity
General applications of D-AAs containing peptides
- anticancer and antiinflammatory agents
- inhibitors of amyloidogenesis
- delivery agents
- antibacterial/antifungal, antibiofilm etc.
1. Marlon H. Cardoso, Elizabete S. Candido. (2017). Peptides containing and retro-inverso peptides: D-amino acids General applications and special focus on antimicrobial peptides.