The Answer
Predicting how the D-enantiomers of naturally occurring proteins and peptides behave hinges on one crucial property: they almost always adopt the exact mirror image three-dimensional structure of their L-counterparts [2]. As such, it might be expected that D-proteins could catalyze the exact same reactions as L-proteins, provided that the stereochemistry of all reactants is accordingly adjusted. This has been confirmed experimentally, for example, by the total synthesis of the enantiomer of an HIV-1 protease [3].
Figure 1: The L- (left, green) and D- (right, cyan) enantiomers of snow flea antifreeze protein (PDB: 3BOG [4]).
Because D-proteins occupy what is essentially the opposite Ramachandran space [5], they conformationally are able to avoid many interactions with natural proteins. For example, it is well known that D-proteins and peptides are highly resistant to degradation by the normal cellular machinery [6]. This is because active sites of proteases are very specific, and many interactions between the enzyme and peptide provide stability [7]. D-peptides cannot fit into the active site, and if they do, they form fewer interactions with the enzyme. However, the chemical functionalities of the side-chains of D-amino acids are the same as for the L-amino acids. Therapeutically, small peptide drugs are highly interesting because interactions between proteins and peptides mediate many cellular processes. However, L-peptides can readily be degraded by cells and often have poor bioavailability when introduced therapeutically [6].
Small D-peptides may, in principle, fare better as drugs. The combination of low degradation potential and exactly the same chemical functionalities as can be made with L-peptides makes them highly attractive to use for therapeutic purposes. In principle, if a D-peptide could be designed to adopt a structure that interacts with a target receptor involved in disease, it would be a highly attractive drug candidate. This principle is used in mirror-image phage display, an elegant technique used to identify viable D-peptides [8] which we discuss here.
Such peptides are actively being researched in the context of a number of diseases, including but not limited to HIV/AIDS [10] and Alzheimer’s disease detection [9]. Here, we focus on the efforts to develop and optimize D-peptides that target a key protein-protein interaction in cancer between the p53 tumor suppressor and MDM2 oncogene product.
November 11, 2016 at 10:39 pm
How are the D-peptides synthesized? Are any found in nature, or is it all in vitro organic chemistry synthesis? You go into the creation of libraries, but not the specific peptides. I feel like you should answer this, as it was part of your question.
November 11, 2016 at 11:47 pm
The questions you ask in the previous page are not all answered in this section. Namely, the question about how D-peptides are synthesized? I think the evolution of the importance/rationale behind why we have D-peptides would be a cool way to contextualize the question and might work better in that section. This way, your talk on drug development will appropriately answer that portion of the question.
The references section detract from the webpage, so I would suggest moving all the references to your last references webpage tab.
The way the answer section is written, it seems that the overall big question is “what is the function of D-peptides?” both in a biological setting and synthetic chemistry setting. The connection between the question you ask and this answer section is not entirely clear and I believe it is because the question is not contextualized. This answer section is very detailed, and I think that better presenting the question could strengthen the flow between these two sections.
November 16, 2016 at 8:15 pm
I agree with everything Lucas and Suraj said. I looked at the paper you cite for the mirror-image phage display and it seems that the D-amino acids are chemically synthesized then used to see if they interact with any L ligands. Based on what you’ve written, I’m assuming you don’t want to focus on chemical synthesis, so I would suggest not including chemical synthesis in your question.
Essentially, your answer goes through whether D-peptides can catalyze opposite chirality reactions, how they function in a cell, and how they can be used therapeutically. Maybe try to reword your question to hit those topics since that’s what your research appears to be about.
You ask a lot of questions, so I wonder if it would be better to organize this section with one question and the answer below so readers don’t lose track. A flow chart may also be a nice addition!
All of the information you do provide is very detailed and well-sourced, which is awesome!
A few other small comments:
-Can you change the spacing on the second paragraph so it matches everything else?
-The first sentence of the third paragraph “Small D-peptides may be a solution.” is a little confusing because you don’t really describe a problem.
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