Peptide Chemistry

NMP/N-methyl-2-pyrrolidone/Pharmasolve
Used to dissolve polymers. Low volatility, flammability & toxicity. Possible reproductive toxicant.
DMSO/Dimethylsulfoxide
Dissolves polar & non-polar compounds. Weakly acidic with High BP. Used in PCR to inhibit secondary DNA structures. Penetrates skin readily and secretes on tongue causing garlic taste.
Thioester
Fmoc is removed in presence of this. Gen. formula: R-C(=O)-S-R’. Can cleave easily when moist. Possible predecessor of ATP. Acetyl-CoA is an example.
HOBt/Hydroxybenzotriazole
Improves yield. Racemization supressor (i.e. prevents formation of enantiomers). White crystalline powder. Explosive when anhydrous.
DMF/Dimethylformamide
Solvent. Penetrates solid support and makes it swell, allowing for penetration of reagents. Removes excess reagents, thus increasing yield. Can undergo photolysis, producing CO and DMamine. Decomposes sometimes, which can be stopped with ice bath. Used in aldehyde synthesis.
Methylpyrrolidine
C5H11N
Fmoc
Protective cap for amines. Can be removed with piperidine or other bases. Preferable in the sense that it doesn’t require the use of HF. Protein is cleaved from resin using TFA. Removal leads to a neutral amine, which causes amines to aggregate. It is fluorescent, which means proteins can be traced once excess is removed.
t-BOC
Protective cap for amines. Cheaper and able to produce more soluble peptides. Also, removal produces charged amines, which prevents aggregation. However, final removal of protein from resin requires HF, which poses a safety risk.
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