Processes for coupling amino acids using...

Details Processes for coupling amino acids using... Processes for coupling amino acids using...

2006-05-16

2006-05-16

Borin, Michael (Department: 1631)

Chemistry: natural resins or derivatives; peptides or proteins;

Peptides of 3 to 100 amino acid residues

Synthesis of peptides

C530S339000, C562S857000

Reexamination Certificate

active

07045592

ABSTRACT:
A process is disclosed for using bis-(trichloromethyl)carbonate (triphosgene), diphosgene or phosgene as efficient and effective coupling reagents during coupling of carbohydrates to peptide chains. This process is particularly useful for the coupling to sterically hindered amino acid residues, or for other difficult couplings. The reagents can be used for the derivatization of peptides by formation of a bond between a free amine on a peptide and a carbohydrate.

REFERENCES:
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Falb et al., “In situgeneration of Fmoc-amino acid chlorides usingbis-(trichloromethyl)carbonate and its utilization for difficult couplings in solid-phase peptide synthesis,” Journal of Peptide Research, vol. 53, No. 5, pp. 507-517 (1999).
Andre et al., “Triphosgene: An Efficient Carbonylating Agent for Liquid and Solid-phase Aza-peptide Synthesis. Application to the Synthsis of Two Aza-analogues of the AChR MIR Decapeptide,”J. Pept. Sci., vol. 3, No. 6, 429-441 (1997).
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