Optimization of solid-phase synthesis of difficult peptide sequences via comparison between different improved approaches

Amino Acids

Volumn 33, Issue 3, 2007, Pages 531-536

  Abdel Rahman, S ^a   El Kafrawy, A ^a   Hattaba, A ^a   Anwer, M F ^a  

^a Zagazig University   (Egypt)

Author keywords

Difficult peptide sequences; Microwave energy; N amide protection; Oligo alanine; Solid phase peptide synthesis

Indexed keywords

ALANINE; ALANINE DERIVATIVE; AMIDE; NITROGEN; OLIGOALANINE; PEPTIDE; PROLINE; UNCLASSIFIED DRUG;

ACYLATION; AMINO ACID SEQUENCE; ARTICLE; COMPARATIVE STUDY; ENERGY; MICROWAVE RADIATION; PRIORITY JOURNAL; SOLID PHASE SYNTHESIS; SOLUBILITY;

ALANINE; AMIDES; AMINES; AMINO ACID SEQUENCE; MICROWAVES; MOLECULAR SEQUENCE DATA; PEPTIDES; PROTEIN STRUCTURE, SECONDARY;

EID: 34548301442     PISSN: 09394451     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00726-006-0387-x     Document Type: Article

References (22)

1. Abdel Rahman S, Goldammer C, Bayer E (1992) A novel solvent system for the synthesis of long chain oligohomopeptides. Peptides: 300-301
2. N Clausen C Goldammer K Jaunch E Bayer 1996 Synthesis of difficult sequences using N-Tmob-protected amino acid derivatives PT Kaumaya RS Hodeges Peptides: chemistry, structure and biology Mayflower Scientific Ltd. Birmingham 71 72
3. H Edelhoch R Berlman M Wilcheck 1969 Fluorescence studies with tyrosyl peptides Biochemistry 7 3893 3900
4. M Erdélyi A Gogoll 2002 Rapid microwave-assisted solid phase peptides synthesis Synthesis 11 1592 1596
5. T Haack M Mutter 1992 Serine derived oxazolidines as secondary structure disrupting, solubilizing building blocks in peptide synthesis Tetrahedron Lett 33 1589 1592
6. BL Hayes 2002 Microwave synthesis, chemistry of the speed of light CEM Publishing Matthews, NC
7. T Johnson M Quibell D Owen RC Sheppard 1993 A reversible protecting group for the amide bond in peptides. Use in the synthesis of difficult sequences J Chem Soc Chem Commun 11 369 372
8. E Kaiser RL Colescott CD Bossinger PI Cook 1970 Color test for the detection of free terminal amino groups in the solid phase synthesis of peptides Anal Biochem 34 595 598
9. SB Kent 1992 R Epton Innovations and perspectives is solid phase synthesis Intercept Ltd. Andover 1
10. th American Peptide Symposium. Pierce Chemical Co., Rockford, II, USA, pp 407-414
11. th American Peptide Symposium. Escom, Leiden, Netherlands, pp 909-910
12. A Loupy 2002 Microwaves in organic synthesis Wiley-VCH Weinheim
13. J Meinhofer M Waki EP Heimer TJ Lambors R Makofske 1979 Solid phase synthesis without repetitive acidolysis Int J Pept Prot Res 13 35 39
14. SCF Milton RC Milton 1990 An improved solid-phase synthesis of a difficult sequence peptide using hexafluoro-2-propanol Int J Pept Prot Res 36 193 196
15. M Mutter H Oppliger A Zier 1992 Solubilizing protecting group in peptide synthesis. Effect of side-chain-attached polyethylene glycol derivatives upon β-sheet formation of model peptides Macromol Chem Rapid Commun 13 151 157
16. th European Peptide Symposium. Scriptor, Copenhagen, pp 660-665
17. rd European Peptide Symposium. Escom Science Publishers BV, Leiden, Netherlands, 1995, pp 173-174
18. RC Sheppard BJ Williams 1982 A new base labile anchoring group for solid phase peptide synthesis Int J Pept Prot Res 20 451 454
19. C Toniolo M Palumbo 1977 Infrared conformational analysis of homo-oligopeptides in the solid state and in solution Biopolymers 16 219 221
20. T Vojkovsky 1995 Detection of secondary amines on solid phase Pept Res 4 236 239
21. T Wöhr F Wahl A Nefzi T Sato M Mutter 1996 Pseudo-proline as a solubilizing, structure-disrupting protection technique in peptide synthesis J Am Chem Soc 118 9218 9227
22. rd International Symposium. Mayflower Scientific Ltd., Birmingham, pp 711-713