Total solid-phase synthesis of the azathiocoraline class of symmetric bicyclic peptides

Chemistry - A European Journal

Volumn 12, Issue 35, 2006, Pages 9001-9009

  Bayó Puxan, Núria ^a   Fernández, Ariadna ^a   Tulla Puche, Judit ^a   Riego, Estela ^a   Cuevas, Carmen ^b   Alvarez, Mercedes ^a   Albericio, Fernando ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b PHARMAMAR S A   (Spain)

Author keywords

Bisintercalators; Coupling reagents; Cyclic peptides; Natural products; On resin cyclization; Peptides

Indexed keywords

CHEMICAL BONDS; CONDENSATION; DRUG PRODUCTS; PROTEINS; SYNTHESIS (CHEMICAL); TUMORS;

BICYCLIC PEPTIDES; BISINTERCALATORS; ON-RESIN CYCLIZATION; PHARMACOKINETIC PROPERTIES; SOLID-PHASE SYNTHESIS;

NITROGEN COMPOUNDS;

AMINO ACID; ANTINEOPLASTIC ANTIBIOTIC; AZATHIOCORALINE; DEPSIPEPTIDE; DNA; FUSED HETEROCYCLIC RINGS; PEPTIDE; THIOL DERIVATIVE;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; CYCLIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METABOLISM; MICROMONOSPORA; STEREOISOMERISM; SYNTHESIS;

AMINO ACIDS; ANTIBIOTICS, ANTINEOPLASTIC; BICYCLO COMPOUNDS, HETEROCYCLIC; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYCLIZATION; DEPSIPEPTIDES; DNA; MICROMONOSPORA; MODELS, CHEMICAL; PEPTIDES; STEREOISOMERISM; SULFHYDRYL COMPOUNDS;

EID: 33845448331     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200600815     Document Type: Article

References (46)

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29. g) for the preparation of hydrophobic peptides usually results in complex crude products: C. Chiva, M. Vilaseca, E. Giralt, F. Albericio, J. Pept. Sci. 1999, 5, 131-140. Unreacted reactive sites were capped with MeOH/DIEA.
30. This strategy also prevents the formation of DKPs. This peptide is prone to undergoing this side-reaction because of the presence of N-methyl amino acids and Gly.
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35. Alternatively, the elongation of the full sequence can be performed stepwise by the same synthetic protocol (Scheme 1). In this case, yields of both strategies were very similar.
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40. + .
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42. These thiocoraline analogues with two different bisintercalation chromophore groups should allow the study of the effects on biological activity both of broken symmetry and of the presence of two distinct chromophore groups.
43. This was prepared from commercially available Boc-D-Dap(Fmoc)OH.
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45. +.
46. For the nomenclature used see: J. Spengler, J. C. Jiménez, E. Giralt. F. Albericio. Nomenclature for Cyclic and Branched Homo- and Heterodetic Peptides. J. Peptide Res. 2005, 65, 550-555.