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Effect of tertiary amine on the carbodiimide-mediated peptide synthesis.

International journal of peptide and protein research (1991-04-01)
M Beyermann, P Henklein, A Klose, R Sohr, M Bienert
ABSTRACT

The effect of tertiary amine (DIEA) on reaction rate and product purity of a carbodiimide/HOBt-mediated peptide synthesis was studied. It was found that very rapid activation can be achieved using carbodiimide/HOBt in non-polar solvents, such as DCM. Although the HOBt is poorly soluble in DCM, the activation proceeds within 2 min, probably forming the HOBt-ester. By such a preactivation followed by a coupling in the presence of DIEA the rate of coupling is comparable with other rapid methods using BOP or TBTU, and no racemization was found in a model coupling (less than 0.1%). For comparison, syntheses of neurotensin by means of different coupling reagents (BOP, TBTU, OPfp-esters) and the DIEA-catalyzed coupling after carbodiimide/HOBt-activation under comparable conditions have shown that these procedures are of the same value in view of coupling efficiency and product purity.

MATERIALS
Product Number
Brand
Product Description

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N,N-Diisopropylethylamine, 99.5%, biotech. grade
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N,N-Diisopropylethylamine, purified by redistillation, 99.5%
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N,N-Diisopropylethylamine, ReagentPlus®, ≥99%
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N-Ethyldiisopropylamine, BASF quality, ≥98.0%
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N-Ethyldiisopropylamine solution, suitable for peptide synthesis, ~2 M in 1-methyl-2-pyrrolidinone