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D-amino acids are conformational mirror images of naturally more occuring L-amino acids. So, instead of making peptides from L-amino acids (L-peptides), they can be made of D-amino acids. Peptides, containing D-amino acids have some pharmacokinetical advantages over all-L-peptides.                   

D-peptide – peptide containing D-amino acids.

D-enantiomer or inverso-peptide – same sequence as L-peptide, but composed of all-D-amino acids and has a mirror conformation.

Retro-inverso-peptide or D-retro-enantiomer – reversed sequence of L-peptide (retro-peptide), but composed of D-amino acids and has a mirror conformation of retro-peptide.

For example (L-aa; d-aa):

L-peptide: H-MDGCEL-OH
Inverso-peptide: H-mdgcel-OH Retro-inverso-peptide: H-lecgdm-OH

Conformationally similar, if terminuses aren’t important: H-MDGCEL-OH and HO-mdgcel-H; H-LECGDM-OH and HO-lecgdm-H.


Advantages of D-peptides:

* less susceptible to proteolytic degradation and thereof are effective for longer time, making D-peptides attractive as pharmaceuticals;

* combination of D-amino acids in the flanking terminal regions with L-amino acids in the core region of the peptide, helps to get drugs with natural bioactivity, but increased bioavailability;

* retro-inverso-peptides show similar binding characteristics as L-peptides with target L-protein and thereof retro-inverso-peptides are attractive alternatives to L-peptides as pharmaceuticals.

* elicit lower immunogenic responses compared to L-peptides.


More to read:  

Briand J-P, et al. 1997. A retro-inverso peptide corresponding to the GH loop of foot-and-mouth disease virus elicits high levels of long-lasting protective neutralizing antibodies. Proc. Natl. Acad. Sci. 94:12545–12550.

Fischer PM. 2003. The design, synthesis and application of stereochemical and directional peptide isomers: a critical review. Curr Protein Pept Sci. 4(5):339-56.

Fujii N and Saito T. 2004. Homochirality and life. Chem Rec. 4(5):267-78.

Guichard G, et al. 1994. Antigenic mimicry of natural L-peptides with retro-inverso-peptidomimetics. Proc Natl Acad Sci U S A. 91(21):9765-9.

Pescarolo MP, et al. 2001. A retro-inverso peptide homologous to helix 1 of c-Myc is a potent and specific inhibitor of proliferation in different cellular systems. FASEB J. 15(1):31-33.

Pinilla C, et al. 1998. All-D peptides recognized by an anti-carbohydrate antibody identified from a positional scanning library. J Mol Biol. 283(5):1013-25.

Schumacher TN, et al. 1996. Identification of D-peptide ligands through mirror-image phage display. Science. 271(5257):1854-7.

Sela M and Zisman E. 1997. Different roles of D-amino acids in immune phenomena. FASEBJ. 11: 449-456.

Sun N, et al. 2012. Mirror image phage display--generating stable therapeutically and diagnostically active peptides with biotechnological means. J Biotechnol. 161(2):121-5

Tugyi R, et al. 2004. Partial D-amino acid substitution: Improved enzymatic stability and preserved Ab recognition of a MUC2 epitope peptide. PNAS. 102:413-418.

Van Regenmortel M HV and Muller S. 1998. D-peptides as immunogens and diagnostic reagents. Curr Opin Biotechnol. 9(4):377-82.

Welch BD, et al. 2010. Design of a potent D-peptide HIV-1 entry inhibitor with a strong barrier to resistance. J Virol. 84(21):11235-44.

Wilkemeyer MF, et al. 2004. Ethanol antagonist peptides: structural specificity without stereospecificity. J Pharmacol Exp Ther. 309(3):1183-9.

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