Preparation of 'side-chain-to-side-chain' cyclic peptides by Allyl and Alloc strategy: Potential for library synthesis

Journal of Peptide Research

Volumn 57, Issue 3, 2001, Pages 250-256

  Grieco, P ^a   Gitu, P M ^a   Hruby, V J ^a  

^a University of Arizona   (United States)

Author keywords

Allyl Alloc strategy; Automated synthesis; Cyclic peptides; Side chain to side chain cyclization; Solid phase synthesis

Indexed keywords

CYCLOPEPTIDE; GLUCAGON DERIVATIVE; PEPTIDE LIBRARY;

ANALYTIC METHOD; ARTICLE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN STRUCTURE;

AMINO ACID SEQUENCE; BIOCHEMISTRY; GLUCAGON; MELANOCYTE-STIMULATING HORMONES; MOLECULAR SEQUENCE DATA; PEPTIDES, CYCLIC;

EID: 0035078547     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1399-3011.2001.00816.x     Document Type: Article

References (31)

1. The cyclic peptides: Structure, conformation, and function
2. Solid-phase synthesis of cyclic peptides
3. Synthesis of glycopeptides, partial structures of biological recognition components
4. Allylic protecting groups and their use in a complex environment. Part II: Allylic protecting groups and their removal through catalytic palladium π-allyl methodology
5. Allylic protection of thiols and cysteine: I: The allyloxycarbonylaminomethyl group
6. Allylic protection of thiols and cysteine: II: The N-[2,3,5,6-tetrafluoro-4-(N′-piperidino)-phenyl], N-allyloxycarbonylaminomethyl (Fnam) group
7. Selective cleavage of the allyl and allyloxycarbonyl groups through palladium-catalyzed hydrostannolysis with tributyltin hydride. Application to the selective protection deprotection of amino acid derivatives and in peptide synthesis
8. On the use of silylated nucleophiles in the palladium catalysed deprotection of allylic carboxylates and carbamates
9. A novel, convenient, three-dimensional orthogonal strategy for solid phase synthesis of cyclic peptides
10. Synthesis of 'Head to Tail' cyclized peptides on solid support by Fmoc chemistry
11. Convergent solid-phase peptide synthesis
12. Allyl-based groups for side-chain protection of amino acids
13. Recent developments in chemical deprotection of ester functional group
14. Solid-phase synthesis of peptides using allylic anchoring groups 2. Palladium-catalysed cleavage of Fmoc-protected peptides
15. A novel allylic anchor for solid-phase synthesis-synthesis of protected and unprotected O-glycosylated mucin-type glycopeptides
16. HYCRON, an allylic anchor for high-efficiency solid phase synthesis of protected peptides and glycopeptides
17. FMOC solid phase synthesis of an endothelin converting enzyme substrate use of allyl ester as the third orthogonal protecting group
18. Automated allyl cleavage for continuous-flow synthesis of cyclic and branched peptides
19. Synthesis of a branched cyclic peptide using strategy employing Fmoc chemistry and two additional orthogonal protecting groups
20. Solid-phase synthesis of 'head-to-tail' cyclic peptides via lysine side-chain anchoring
21. New allylic group acceptors for palladium catalyzed removal of allylic protection and transacylation of allyl carbamates
22. 3/carboxy-activated amino acids
23. Solid phase-mediated cyclization of head-to-tail peptides: Problems associated with side chain anchoring
24. 3/carboxy-activated amino acid
25. Use of Alloc-amino acids in solid-phase peptide synthesis. Tandem deprotection-coupling reactions using neutral conditions
26. Synthesis of cyclic peptides by solid phase methodology
27. Synthesis of side-chain to side-chain cyclized peptide analogs on solid supports
28. Applications of BOP reagent in solid-phase synthesis. 2. Solid-phase side-chain to side-chain cyclizations using BOP reagent
29. Potent and prolonged acting cyclic lactam analogues of α-melanotropin. Design based on molecular dynamics
30. Solid-phase synthesis of cyclic homodetic peptides
31. Convenient synthesis of a head-to-tail cyclic peptide containing an expanded ring