Synthesis of peptide-N-alkylamides on a new PS-TTEGDA polymer support using photolabile anchoring group

Tetrahedron

Volumn 55, Issue 34, 1999, Pages 10437-10446

  Kumar, K S ^a   Pillai, V N Rajasekharan ^b  

^a RAJIV GANDHI CENTRE FOR BIOTECHNOLOGY   (India)

^b MAHATMA GANDHI UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID DERIVATIVE; AMIDE; BENZOIC ACID DERIVATIVE; ETHYLENE GLYCOL DERIVATIVE; PEPTIDE; POLYMER; POLYSTYRENE;

ARTICLE; CHEMICAL MODIFICATION; MOLECULAR INTERACTION; PEPTIDE SYNTHESIS; PHOTOLYSIS; POLYMERIZATION; PRIORITY JOURNAL; PURIFICATION; SOLVATION;

EID: 0033588288     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00569-4     Document Type: Article

References (26)

1. Abbreviations used for amino acids follow the IUPAC-TUB Commission of Biochemical Nomenclature in Eur. J. Biochem. 1984, 138, 9-37; J.Biol. Chem. 1989, 264, 663-673. The following additional abbreviations are used: DCM, dichloromethane; DMF, dimethylformamide; RP-FPLC, reverse phase-fast protein liquid chromatography; HOBt, l-hydroxybenzotriazole; IR, infrared; MeCN, acetonitrile; MeOH, methanol; NMP, N-methyl-2-pyrrolidinone; EtOH, ethanol; NMR, nuclear magnetic resonance; CP-MAS,cross polarised-magic angle spin; TFA, trifluoroacetic acid; THF, tetrahydrofuran; KBr, potassium bromide, NBS, N-bromosuccinimide, Boc, t-butyloxycarbonyl; DIEA, diisopropylethylamine
2. Abbreviations used for amino acids follow the IUPAC-TUB Commission of Biochemical Nomenclature in Eur. J. Biochem. 1984, 138, 9-37; J.biol. Chem. 1989, 264, 663-673. The following additional abbreviations are used: DCM, dichloromethane; DMF, dimethylformamide; RP-FPLC, reverse phase-fast protein liquid chromatography; HOBt, l-hydroxybenzotriazole; IR, infrared; MeCN, acetonitrile; MeOH, methanol; NMP, N-methyl-2-pyrrolidinone; EtOH, ethanol; NMR, nuclear magnetic resonance; CP-MAS,cross polarised-magic angle spin; TFA, trifluoroacetic acid; THF, tetrahydrofuran; KBr, potassium bromide, NBS, N-bromosuccinimide, Boc, t-butyloxycarbonyl; DIEA, diisopropylethylamine
3. Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 2149-2154.
4. Gutte, B.; Merrifield, R. B. J. Biol. Chem. 1971, 246, 1922-1941.
5. Pillai, V. N. R.; Mutter, M. Top. Curr. Chem. 1982, 35, 161-214.
6. Atherton, E.; Clive, D. L. J.; Sheppard, R. C. J. Am. Chem. Soc. 1975, 97, 6584-6585.
7. Atherton, E.; Brown, E.; Sheppard, R. C. J. Chem. Soc. Chem. Commun. 1981, 1151-1152.
8. Meldel, M. Tetrahedron Lett. 1992, 33, 3077-3080.
9. Kempe, M; Barany, G. J. Am. Chem. Soc. 1996, 118, 7083-7093.
10. Renil, M; Nagaraj, R.; Pillai, V. N. R. Tetrahedron 1994, 50, 6681-6688.
11. Dawkins, J. V. Aqueous Suspension Polymerisation. In: Comprehensive Polymer Science, Vol.4.; Eastmond, G. C.; Ledwith, A.; Segwatt, R. P. Eds.; Pergamon Press: Oxford, 1989, pp 231 241
12. Stimson, E. R.; Meinwald, Y. E.; Mintelion, G. T.; Scheraga, H. A. Int. J. Pept. Protein Res. 1986, 27, 569-573.
13. Mammi, S.; Goodman, M. Int. J. Pept. Protein Res. 1986, 28, 29-34.
14. Bodanziky, M.; Martinez, J. Synthesis. 1981, 5, 333.
15. Ajayaghosh, A.; Pillai, V. N. R. J. Org. Chem. 1987, 52, 5714-5717.
16. Rich, D. H.; Gurwara, S. K. J. Am. Chem. Soc. 1975, 97, 1575-1578.
17. Pillai V. N. R. In Organic Photochemistry, Vol. 9, Psdwa, A.Ed.; Marcel Dkker, New York, 1987; pp. 225 312.
18. Rich, D. H.; Gurwara, S. K. Tetrahedron Lett. 1975, 301-303.
19. Feinberg, R. S.; Merrifield, R. B. Tetrahedron 1974, 30, 3209-3212.
20. nd Edn, Pierce Chemical Co.; Rockford, IL, 1984; 54-113.
21. Gisin, B. F. Anal. Chem. Acta. 1972, 58, 248-249.
22. Morrison, H. A. The Chemistry of Nitro and Notroso Groups; Feuer, H. Ed.; Part 1, Wiley, New York, 1970; p. 185.
23. Patchornik, A.; Amit, B.; Woodwared, R. B. J. Am. Chem. Soc. 1970, 92, 6333-6337.
24. Yip, R, W.; Sharma, D. K.; Giasson, R.; Gravel, D. J. Phys. Chem. 1985, 89, 5328-5331.
25. Kaiser, E.; Cotescott, R.; Bossinger, C. D.; Cook, P. I. Anal. Biochem. 1970 34, 54-113.
26. nd Edn; Willy, New York, p377.