Active carbonate resins for solid-phase synthesis through the anchoring of a hydroxyl function. Synthesis of cyclic and alcohol peptides

Tetrahedron Letters

Volumn 38, Issue 5, 1997, Pages 883-886

  Alsina, Jordi ^a   Chiva, Cristina ^a   Ortiz, Marta ^a   Rabanal, Francesc ^a   Giralt, Ernest ^a   Albericio, Fernando ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

OCTREOTIDE;

ARTICLE; METHODOLOGY; PEPTIDE SYNTHESIS; PHOTOLYSIS; REACTION ANALYSIS;

EID: 0031033427     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02431-8     Document Type: Article

References (42)

1. Abbreviations not defined in the text: Acm, acetamidomethyl; Boc, tert.-butyloxycarbonyl; BAL, backbone amide linker; Bzl, benzyl; CDI, carbonyl imidazole; CI-MS, chemical ionization mass spectrometry; CIZ, chlorobenzyloxycarbonyl; DIEA, N,N-diisopropylethylamine; DEAD, diethyl azodicarboxylate; DIPCDI, N,N-diisopropylcarbodiimide; DMAP, N,N-dimethyl-4-aminopyridine; DMF, N,N-dimethylformarnide; DMSO, dimethylsulfoxide; ES-MS, electrospray mass spectrometry; Fmoc, 9-fluorenylmethyloxycarbonyl; For, formyl; HOAc, acetic acid; HOAt, 7-aza-1-hydroxybenzotriazole; HOBt, 1-hydroxybenzotriazole; HPLC, high performance liquid chromatography; PPTS, pyridinium p-toluensulfonate; PS, polystyrene; PyAOP, 7-aza-benzotriazol-1-yl-oxy-tris(pyrrolidino)-phosphonium hexafluorophosphate; R(PAL), tris(alkoxybenzyl) N-alkylamide; Su, succinimidyl; tBu, tert.-butyl; TFA, trifluoroacetic acid; TFMSA, trifluoromethanesulfonic acid; THF, tetrahydrofuran; Thr-oh, threoninol. Amino acid symbols denote L-configuration unless indicated otherwise.
2. Lloyd-Williams, P.; Albericio, F.; Giralt, E. In Chemical Approaches to the Synthesis of Peptides and Proteins; CRC: Boca Raton, FL, 1997.
3. Oligonucleotides and Analogues. A Practical Approach (Eckstein, F., ed.) IRL Press: Oxford, 1991.
4. Hermkens, P.H.H.; Ottenheijm, H.C.J.; Rees, D. Tetrahedron 1996, 52, 4527-4554.
5. Handles are defined as bifunctional spacers, or linkers, which incorporate on one end features of a selectively removable protecting group and contain a second end which serves to achieve the required anchoring to the solid support as a separate chemical step. Barany, G.; Albericio, F. In Peptides. Chemistry, Structure and Biology. Proceedings of the Thirateenth American Peptide Symposium (Hodges, R.S.; Smith, J.A., eds.) ESCOM: Leiden, The Netherlands 1994; pp 1078-1079.
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17. (h) Aviño, A.; Güimil-Garcia, R.; Albericio, F.; Mann, M.; Wilm, M.; Neubauer, G.; Eritja, R. Bioorg. Med. Chem. 1996, in press.
18. (a) Barlos, K.; Chatzi, O.; Gatos, D.; Stavropoulos, G. Int. J. Peptide Protein Res. 1991, 37, 513-520;
19. (b) Wenschuh, H.; Beyermann, M.; Haber, H.; Seydel, J. K.; Krause, E.; Bienert, M.; Carpino, L. A.; El-Faham, A.; Albericio, F. J. Org. Chem. 1995, 60, 405-410.
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21. (a) Swistok, J.; Tilley, J.W.; Danho, W.; Wagner, R.; Mulkerins, K. Tetrahedron Lett. 1989, 30, 5045-5048;
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26. 4-Hydroxymethyl-PS-resin was obtained from Advanced ChemTech (Louisville, KY); nominal loading: 1.35 mmol/g.
27. 4-Hydroxymethyl-Nbb-PS-resin was prepared from 4-hydroxymethyl-3-nitrobenzoic acid [(a) Giralt, E.; Albericio, F.; Pedroso, E.; Granier, C.; van Rietschoten, J. Tetrahedron 1982, 38, 1193-1208;
28. (b) Barany, G.; Albericio, F. J. Am. Chem. Soc. 1985, 107, 4936-4942;
29. Lloyd-Williams, P.; Gairí, M.; Albericio, F.; Giralt, E. Tetrahedron 1991, 47, 9867-9880] and MBHA-resin, and the loading was 0.56 mmol/g.
30. 4, and concentration in vacuo. Boc-Ser-OAllyl (95% yield) obtained as an oil and Boc-Tyr-OAllyl (92% yield) obtained as a solid gave a single peak in HPLC and were characterized by CI-MS.
31. Mitchell, A. R.; Erickson, B. W.; Ryabtsev, M. N.; Hodges, R. S.; Merrifield, R. B. J. Am. Chem. Soc. 1976, 98, 7357-7362.
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33. Albericio, F.; Barany, G. Int. J. Peptide Protein Res. 1985, 26, 92-97.
34. Amino acid hydrolysis was carried out after the incorporation of a second protected amino acid in the sequence, since Tyr and Ser can be destroyed during the acid hydrolysis, and Thr-oh was not detected in the amino acid autoanalyzer.
35. 2 (5×30 sec), amino acid coupling (30 min) with Boc-amino acids (5 equiv), HOBt (5 equiv) and DIPCDI (5 equiv) in DMF, and DMF washing (5×30 sec).
36. (a) Lloyd-Williams, P.; Jou, G.; Albericio, F.; Giralt, E. Tetrahedron Lett. 1991, 32, 4207-4210.
37. (b) Kates, S.A.; Daniels, S.B.; Albericio, F. Anal. Biochem. 1993, 212, 303-310.
38. (a) Carpino, L.A. J. Am. Chem. Soc. 1993, 115, 4397-4398;
39. (b) Carpino, L.A.; El-Faham, A.; Minor, C.A.; Albericio, F. J. Chem. Soc., Chem. Commun. 1994, pp. 201-203.
40. (a) García-Echeverría, C.; Albericio, F.; Pons, M.; Barany, G.; Giralt, E. Tetrahedron Lett. 1989, 30, 2441-2444;
41. (b) Albericio, F.; Hammer, R. P.; García-Echeverría, C.; Molins, M. A.; Chang, J. L.; Munson, M.; Pons, M.; Giralt, E.; Barany, G. Int. J. Peptide Protein Res. 1991, 37, 402-413.
42. Ellman, J. A. Acc. Chem. Res. 1996, 29, 132-143.