Protecting groups for asparagine and glutamine in peptide synthe

Details Protecting groups for asparagine and glutamine in peptide synthe Protecting groups for asparagine and glutamine in peptide synthe

1989-02-27

1990-06-19

Reamer, James H.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

560 39, 562448, C07C12506

Patent

active

049355368

ABSTRACT:
Trialkoxybenzyl (Taob) protected asparagine and glutamine, a method of synthesis and a method of use are provided. The Taob protected Asn and Gln have the following formulae: ##STR1## wherein Z is an alkyl group having from 1 to 10 carbon atoms; X and W are any .alpha.-protecting group which can be selectively removed while maintaining Taob intact; Y is H or any group sufficiently active or activatable to react with NH.sub.2 -- or NH.dbd. to generate an amide bond; n is 1 for asparagine or 2 for glutamine. These derivatives are stable in solution, have good solubility in organic solvents and couple directly without side reactions.

REFERENCES:
patent: 2873294 (1959-02-01), Kline
patent: 3903147 (1975-02-01), Kyncl et al.
patent: 4716232 (1987-12-01), Teransky
Weygand et al., Chem. Ber., vol. 101: 3642-3648 (1968).
Weygand et al., Chem. Ber., 101, pp. 3623-3641 (1968).

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