Urethane-protected amino acid-N-carboxyanhydrides

Details Urethane-protected amino acid-N-carboxyanhydrides Urethane-protected amino acid-N-carboxyanhydrides

1989-07-13

1991-07-02

Schain, Howard E.

Chemistry: natural resins or derivatives; peptides or proteins;

Peptides of 3 to 100 amino acid residues

Synthesis of peptides

530333, 530334, 530337, 548227, 548183, 548188, 544 97, 544 54, 540488, C07K 100, C07D27700, C07D27900, C07D28100

Patent

active

050286935

ABSTRACT:
Urethane-protected NCAs and MTAs are prepared by reacting an NCA or NTA with a haloformate in an inert diluent, under anhydrous conditions and in the presence of a tertiary nitrogen-containing base having an atom or functional group sufficiently electron rich and positioned relative to the nitrogen of said base so as to render said atom or group capable of complexing with the H--N< group of said N-carboxyanhydride or N-thiocarboxyanhydride but able to generate N-carboxyanhydride or N-thiocarboxyanhydride anionic complexes capable of reacting with the haloformate.

REFERENCES:
Benoiton, N., et al., Int. J. Peptide Protein Reg., 31: 577-580, 1988.
Chen, F., et al., Con. J. Chem., 65(3): 619-653, 1987.
Ahiyama, M., Tetrahedron Letters, 28: 2599-2600, 1979.
Shimizu, K., Bull. Chem. Soc. Jpn., 57: 495-499, 1984.
Hirschmann, R., JACS, 93(11): 2746-2754, 1971.
Halstrom, J., Peptides (Eur. Peptide Symp., 12th, 1972), 1973.
Bodanszky, M., Principles of Peptide Synthesis, Springer-Verlag, N.Y.; 85-86, 1984.

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