Use of benzyloxycarbonyl (Z)-based fluorophilic tagging reagents in the purification of synthetic peptides

Tetrahedron Letters

Volumn 43, Issue 43, 2002, Pages 7809-7812

  Filippov, Dmitri V ^a   Van Zoelen, Dirk J ^a   Oldfield, Steven P ^a   Van Der Marel, Gijs A ^a   Overkleeft, Herman S ^a   Drijfhout, Jan W ^b   Van Boom, Jacques H ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

^b LEIDEN UNIVERSITY MEDICAL CENTER   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYL CHLOROFORMATE; BENZYL DERIVATIVE; CARBONYL DERIVATIVE; REAGENT; SYNTHETIC PEPTIDE; UNCLASSIFIED DRUG;

ARTICLE; MASS SPECTROMETRY; PEPTIDE SYNTHESIS; PHASE TRANSITION; PURIFICATION; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

EID: 0037152304     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01723-9     Document Type: Article

References (21)

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13. 2: C, 38.27; H, 2.20. Found: C, 37.99; H, 2.45.
14. 2 group of lysine.
15. 2 group of lysine.
16. The Mtt-group (Aletras, A.; Barlos, K.; Gatos, D.; Koutsogianni, S.; Mamos, P. Int. J. Peptide Protein Res. 1995, 45, 488-496), which can be cleaved with 1% TFA, was used for lysine side chain protection to offset potential solubility problems inherent to partially protected oligopeptides.
17. +.
18. 2O/1% aq. TFA over 2 CV (column volumes), then with a gradient up to 90:10 MeOH/1% aq. TFA over 7 CV and finally with MeOH for 10 CV. In the case of peptide 18 a gradient of trifluoroethanol from 25% to 90% in 0.05% aq. TFA over 13 CV was applied.
19. 2O (98/2) for 1 h at 20°C.
20. For a recent example of a heavy-fluorous Z-based protection, see: Schwinn D., Bannwarth W. Helv. Chim. Acta. 85:2002;255-264.
21. Preliminary experiments indicated that a Z-based fluoroalkylated tag containing two fluorophilic tails was readily accessible via the Heck cross-coupling procedure.