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To illustrate the impact of suboptimal coupling yields for a given synthesis, consider the case where each coupling step were to have at least 99% yield: this would result in a 77% overall crude yield for a 26-amino acid peptide (assuming 100% yield in each deprotection); if each coupling were 95% efficient, the overall yield would be 25%.
DEPBT (3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one) is a peptide coupling reagent used in peptide synthesis.It shows remarkable resistance to racemization. [1]Fmoc-Dab(Mtt)-OH, a commercially available amino acid building block for solid-phase peptide synthesis (SPPS), was proven to undergo rapid lactamization, instead of reacting with the N-terminal end of the peptide.
HBTU (Hexafluorophosphate Benzotriazole Tetramethyl Uronium) is a coupling reagent used in solid phase peptide synthesis. It was introduced in 1978 and shows resistance against racemization. [3] [4] It is used because of its mild activating properties. [5]
HATU is commonly encountered in amine acylation reactions (i.e., amide formation). Such reactions are typically performed in two distinct reaction steps: (1) reaction of a carboxylic acid with HATU to form the OAt-active ester; then (2) addition of the nucleophile (amine) to the active ester solution to afford the acylated product.
PyAOP ((7-Azabenzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate) is a reagent used to prepare amides from carboxylic acids and amines in the context of peptide synthesis. [1] It can be prepared from 1-hydroxy-7-azabenzotriazole (HOAt) and a chlorophosphonium reagent under basic conditions. [ 2 ]
PyBOP (benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate) is a reagent used to prepare amides from carboxylic acids and amines in the context of peptide synthesis. [3] It can be prepared from 1-hydroxybenzotriazole and a chlorophosphonium reagent under basic conditions. [ 4 ]
N,N ′-Diisopropylcarbodiimide is a carbodiimide used in peptide synthesis. [1] [2] As a liquid, it is easier to handle than the commonly used N,N ′-dicyclohexylcarbodiimide, a waxy solid. In addition, N,N ′-diisopropylurea, its byproduct in many chemical reactions, is soluble in most organic solvents, a property that facilitates work-up.
BOP (benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate) is a reagent commonly used for the synthesis of amides from carboxylic acids and amines in peptide synthesis. [ 1 ] [ 2 ] It can be prepared from 1-hydroxybenzotriazole and a chlorophosphonium reagent under basic conditions. [ 3 ]