Reactions And Reagents O.p Agarwal.pdf
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In the coupling of peptides, the use of the BOP reagent with EDCI (1-ethyl-3-(3-dimethylaminopropyl)carbodiimide) and HOBt (1-hydroxy-benzotriazole) is recommended. In the case of non-aromatic amino acids, EDCI and HOBt should be used instead of NEDCI. When using HOBt and EDCI for the synthesis of peptides the use of L-lysine is recommended. If the stereochemistry of the coupling is important, using the D-lysine should be done. However, the use of L-lysine is still the recommended use. When coupling carboxylic acids to an amine, the use of BOP is important to prevent the formation of the corresponding esters. The use of EDCI (1-ethyl-3-(3-dimethylaminopropyl)carbodiimide) is recommended in the case of aromatic carboxylic acids. If the peptide is being synthesized in solution, this reagent should be used to avoid side reactions and the formation of amides. If the coupling is to be done in a solid phase, then BOP should be used instead of EDCI. For peptide sequencing, EDCI can be used. In peptide sequencing EDCI is beneficial because it allows for the formation of the amide bond without the use of a protecting group. EDCI is also important in the case of peptide cleavage, where it is used to cleave the peptide from the resin. Additionally, it is used with ammonium hydroxide solution.
CHO (cyclohexyloxycarbodiimide) reagent is a reagent that forms a reactive carbodiimide which reacts well with carboxylic acids. This reagent is used to couple amino acids to peptides. It is also used as a catalyst for the coupling of amino acids to peptides. This reagent is also useful for peptide conjugation in protein-protein interactions. The disadvantage of this reagent is that it liberates HMPA which is carcinogenic. The use of DCC (dicyclohexylcarbodiimide) is recommended for use with peptides and proteins.
Chloramine-T (chloraminem-thiocarbonylcyanide) is an organic reagent that was used to oxidize peptides that contain a thioester. It is used to form an amide or an ester. For example, this reagent is used to oxidize thioesters to form amides for the synthesis of peptides.[6] Chloramine-T is considered to be too toxic to be used clinically. In addition, thiols are easily oxidized which can result in many undesirable side reactions.[6]
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