An important side reaction using the thiol, 3,6-dioxa-1,8-octanedithiol (DODT), in 9-fluorenylmethoxycarbonyl-based solid phase peptide synthesis

Journal of Peptide Science

Volumn 20, Issue 3, 2014, Pages 186-190

  Harris, Paul W R ^a   Kowalczyk, Renata ^a   Yang, Sung Hyun ^a   Williams, Geoffrey M ^a   Brimble, Margaret A ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

Author keywords

3,6 dioxa 1,8 ocatanedithiol; alkylation; methionine; peptide cleavage

Indexed keywords

3,6-DIOXA-1,8-OCATANEDITHIOL; ALKYLATION; METHIONINE; PEPTIDE CLEAVAGE;

ETHYL ETHERS; FLUORENES; MASS SPECTROMETRY; SOLID-PHASE SYNTHESIS TECHNIQUES; SULFHYDRYL COMPOUNDS;

EID: 84893956891     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.2595     Document Type: Article

References (16)

1. Amblard M, Fehrentz JA, Martinez J, Subra G,. Methods and protocols of modern solid phase peptide synthesis. Mol. Biotechnol. 2006; 33: 239-254.
2. Schnolzer M, Alewood P, Jones A, Alewood D, Kent SBH,. In situ neutralization in boc-chemistry solid phase peptide synthesis-rapid, high yield assembly of difficult sequences. Int. J. Pept. Res. Ther. 2007; 13: 31-44.
3. Fields GB, Noble RL,. Solid-phase peptide-synthesis utilizing 9-fluorenylmethoxycarbonyl amino-acids. Int. J. Pept. Protein Res. 1990; 35: 161-214.
4. Guy CA, Fields GB,. In Methods Enzymol, Fields GB, (ed.). Academic Press: Waltham, MA, 1997; 67-83.
5. King DS, Fields CG, Fields GB,. A cleavage method which minimizes side reactions following Fmoc solid-phase peptide-synthesis. Int. J. Pept. Protein Res. 1990; 36: 255-266.
6. Huang H, Rabenstein DL,. A cleavage cocktail for methionine-containing peptides. J. Pept. Res. 1999; 53: 548-553.
7. Teixeira A, Benckhuijsen WE, de Koning PE, Valentijn ARPM, Drijfhout JW,. The use of DODT as a non-malodorous scavenger in FMOC-based peptide synthesis. Protein Pept. Lett. 2002; 9: 379-385.
8. Harris PWR, Yang SH, Brimble MA,. An improved procedure for the preparation of aminomethyl polystyrene resin and its use in solid phase (peptide) synthesis. Tetrahedron Lett. 2011; 52: 6024-6026.
9. Harris PWR, Williams GM, Shepherd P, Brimble MA,. The synthesis of phosphopeptides using microwave-assisted solid phase peptide synthesis. Int. J. Pept. Res. Ther. 2008; 14: 387-392.
10. Noble RL, Yamashiro D, Li CH,. Studies on pituitary lactogenic hormone.39. Synthesis of a nonadecapeptide corresponding to residues 37-55 of ovine prolactin-detection and isolation of sulfonium form of methionine-containing peptides. J. Am. Chem. Soc. 1976; 98: 2324-2328.
11. Bodanszky M, Bednarek MA,. Experiments on the protection of the thioether in methionine. Int. J. Pept. Protein Res. 1982; 20: 408-413.
12. Chassaing G, Lavielle S, Marquet A,. Transformation of methionine into S-tert-butylhomocysteine-application to a methionine-containing peptide-substance-P. J. Org. Chem. 1983; 48: 1757-1760.
13. Naider F, Bohak Z,. Regeneration of methionyl residues from their sulfonium salts in peptides and proteins. Biochemistry 1972; 11: 3208-3211.
14. Doi JT, Luehr GW,. Thioether protection via selectively cleavable sulfonium salts. Tetrahedron Lett. 1985; 26: 6143-6146.
15. Gundlach HG, Moore S, Stein WH,. Reaction of iodoacetate with methionine. J. Biol. Chem. 1959; 234: 1761-1764.
16. Auvray P, Knochel P, Normant JF,. 3-Bromo-2-tert-butylsulfonyl-1-propene- a versatile multi-coupling reagent.1. Tetrahedron 1988; 44: 4495-4508.