Method for the production of cyclic molecules

Details Method for the production of cyclic molecules Method for the production of cyclic molecules

2004-07-30

2011-11-22

Ford, Allison M. (Department: 1651)

Chemistry: natural resins or derivatives; peptides or proteins;

Peptides of 3 to 100 amino acid residues

Synthesis of peptides

C530S317000, C435S068100

Reexamination Certificate

active

08063181

ABSTRACT:
The invention at hand describes a method for the cyclization of peptides and proteins in which linear thioesters serve as substrates. The cyclization is catalyzed by thioesterase domains of NRPS or PKS cyclases. The substrates according to the present invention are composed of one linear peptide on which a charge-stabilized aromatic, heteroaromatic or araliphatic leaving group is bound. These substrates lead to higher yields and reaction rates than linear peptides able to be cyclized with methods known so far and, furthermore, allow the cyclization of such peptides which were previously not able to be cyclized.

REFERENCES:
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patent: WO 01/05815 (2001-01-01), None
patent: WO 02/085401 (2002-10-01), None
Sieber, SA et al. Peptidyl thiophenols as substrates for nonribosomal peptide cyclases. Angew. Chem. 2004. 43:493-498. Published online Jan. 14, 2004.
J. Grunewald et al., “Chemo- and Regioselective Peptide Cyclization Triggered by the N-Terminal Fatty Acid Chain Length: The Recombinant Cyclase of the Calcium-Dependent Antibiotic fromStreptomyces coelicolor”; Biochemistry2004, 43, 2915-2925.
R. Kohli et al., “Generality of Peptide Cyclization Catalyzed by Isolated Thioesterase Domains of Nonribosomal Peptide Synthetases”,Biochemistry2001, 40, 7099-7108.
T. Keating et al., “Chain Termination Steps in Nonribosomal Peptide Synthetase Assembly Lines: Directed Acyl-S-Enzyme Breakdown in Antibiotic and Siderophore Biosynthesis”,Chembiochem2001, 2, 99-107.
C. Tseng et al., “Characterization of the Surfactin Synthetase C-Terminal Thioesterase Domain as a Cyclic Depsipeptide Synthase”,Biochemistry2002, 47, 13350-13359.

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