Efficient, racemization-free peptide coupling of N-alkyl amino acids by using amino acid chlorides generated in situ - Total syntheses of the cyclopeptides cyclosporin o and omphalotin a

Angewandte Chemie - International Edition

Volumn 41, Issue 24, 2002, Pages 4661-4663

  Sewald, Norbert ^a  

^a BIELEFELD UNIVERSITY   (Germany)

Author keywords

Amino acids; Bioorganic chemistry; Coupling reagent; Peptides; Total synthesis; Triphosgene

Indexed keywords

CHLORINE COMPOUNDS; SYNTHESIS (CHEMICAL);

PEPTIDE COUPLING;

AMINO ACIDS;

AMINO ACID; ANTIFUNGAL AGENT; ANTIINFLAMMATORY AGENT; CHLORIDE; CYCLOPEPTIDE; CYCLOSPORIN; CYCLOSPORIN DERIVATIVE; CYCLOSPORIN O; IMMUNOSUPPRESSIVE AGENT; OMPHALOTIN A; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ANTIFUNGAL ACTIVITY; ANTIINFLAMMATORY ACTIVITY; CHEMISTRY; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ISOMERISM; PROTEIN CONFORMATION; SHORT SURVEY; SYNTHESIS;

AMINO ACID SEQUENCE; AMINO ACIDS; CHLORIDES; CYCLOSPORINS; ISOMERISM; PEPTIDES, CYCLIC; PROTEIN CONFORMATION;

EID: 0037122171     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200290008     Document Type: Short Survey

References (9)

1. B. Them, J. Rudolph, G. Jung, Tetrahedron Lett. 2002, 43, 5013-5016.
2. B. Thern, J. Rudolph, G. Jung, Angew. Chem. 2002, 114, 2401-2403; Angew. Chem. Int. Ed. 2002, 41, 2307-2309.
3. B. Thern, J. Rudolph, G. Jung, Angew. Chem. 2002, 114, 2401-2403; Angew. Chem. Int. Ed. 2002, 41, 2307-2309.
4. N. Sewald, H.-D. Jakubke, Peptides: Chemistry and Biology, Wiley-VCH, Weinheim, 2002.
5. E. Falb, Y. Yechezkel, Y. Salitra, C. Gilon, J. Pept. Res. 1999, 53, 507-517.
6. H. Eckert, B. Forster, Angew. Chem. 1987, 99, 922-923; Angew. Chem. Int. Ed. Engl. 1987, 26, 894-895.
7. H. Eckert, B. Forster, Angew. Chem. 1987, 99, 922-923; Angew. Chem. Int. Ed. Engl. 1987, 26, 894-895.
8. L. A. Carpino, M. Beyermann, H. Wenschuh, M. Bienett, Acc. Chem. Res. 1996, 29, 268-274.
9. L. A. Carpino, A. El-Faham, Tetrahedron 1999, 55, 6813-6830.