Protected derivatives of tryptophan, processes for their prepara

Details Protected derivatives of tryptophan, processes for their prepara Protected derivatives of tryptophan, processes for their prepara

1992-05-27

1994-04-05

Lee, Mary C.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548454, 548495, 530333, 530337, C07F 906, C07D20918

Patent

active

053006518

ABSTRACT:
A derivative of tryptophan is provided wherein the NH-group of the tryptophan indole nucleus is protected with tert.-butyloxycarbonyl (BOC) and the .alpha.-amino group is protected by 9-fluorenyl-methyloxy-carbonyl (FMOC). The carboxylic acid group of the tryptophan derivative may comprise a free COOH group, may be modified with a protecting or activating group, or may comprise an acyl group bonded to another chemical moiety, such as a polymer, another amino acid, a dipeptide, a polypeptide, or a protein. The tryptophan derivative is useful in the preparation of dipeptides, polypeptides or proteins containing at least one tryptophan-derived amino acid residue.

REFERENCES:
Tetrahedron, (Incl. Tetrahedron Reports), vol. 44 No. 3, 1 Mar. 1988, Oxford GB, pp. 843-857 E. Atherton et al.
"Peptide Synthesis, Part 10. Use of Pentafluorophenyl esters of Flourenyl Methoxycarbonylamino Acids in Solid Phase Peptide Synthesis".
Journal of The American Chemical Society, vol. 94, No. 8, 19 Apr. 1972, Gaston, Pa. US pp. 2855-2859, D. Yamashiro et al.
"The Use of N-alpha, N-im bis (Tert-butyloxycarbonyl)histidine and n-alpha-2-(p-biphenyly)isopropyloxycarbonyl-N-im-tertbutyloxcarbonylhistid ine in the solid-phase synthesis of histidine-containing peptides".
Chemical Abstracts, vol. 115, No. 19, 11 Nov. 1990, Abstract No. 20851OS, H. Kalbacher et al.
"Acid labile protection of histidine and arginine in spps using adpoc derivatives" & Pept. 1990, Proc, Eur. Pept. Symp. 21st 1990 Leiden.
Tetrahedron Letters, vol. 28, No. 48, pp. 6031-6034, 1987, Sieber et al. "Protection of Histidine In Peptide Synthesis: A Reassessment of the Trityl Group".
Chem. Soc. Chem. Commun., 1984, Frazen et al., Synthesis, Properties, and Use of N.sup.in -Boc-tryptophan Derivatives, pp. 1699-1700.

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