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This would compete with the intended peptide coupling reaction, resulting in low yield or even complete failure to synthesize the desired peptide. [citation needed] Two principle protecting group schemes are typically used in solid phase peptide synthesis: so-called Boc/benzyl and Fmoc/tert-butyl approaches. [2]
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]
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.
N,N′-Dicyclohexylcarbodiimide (DCC or DCCD) [1] is an organic compound with the chemical formula (C 6 H 11 N) 2 C. It is a waxy white solid with a sweet odor. Its primary use is to couple amino acids during artificial peptide synthesis.
In the realm of peptide synthesis, this product may be treated with an amine such as that found on an amino acid to release the imidazole group and couple the peptides. The side products, carbon dioxide and imidazole, are relatively innocuous. [5] Racemization of the amino acids also tends to be minimal, reflecting the mild reaction conditions.
In one important reaction type, a main group organometallic compound of the type R-M (where R = organic group, M = main group centre metal atom) reacts with an organic halide of the type R'-X with formation of a new carbon-carbon bond in the product R-R'. The most common type of coupling reaction is the cross coupling reaction. [1] [2] [3]