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Fmoc-L-trans-Hyp(Nfb)-OH
Chemical name: N-alpha-(9-Fluorenylmethyloxycarbonyl)-O-(nonafluoro-t-butyl)-trans-L-hydroxyproline // Synonyms: Fmoc-Hyp(nonafluoro-t-butyl)-OH (trans), (2S,4R)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-(1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-yloxy)pyrrolidine-2-carboxylic acidFmoc-L-Hyp(Nfb)-OH (t rans), Fmoc-L-Hyp(Nfb)-OH (2S,4R), Fmoc-trans-Hyp(
- Product code:FAA4560
- CAS No.:1622172-75-1
- Formula:C24H18F9NO5
- Molecular weight:571.39 g/mol
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description
The nonafluoro-t-butyl group (Nfb) equips the proline moiety with both polarity and hydrophobicity. It is stable to standard SPPS cleavage conditions for Wang typical linkers, like 90% TFA/10% scavengers.
references
(2S,4R)- and (2S,4S)-Perfluoro-tert-butyl 4-Hydroxyproline: Two Conformationally Distinct Proline Amino Acids for Sensitive Application in 19F NMR; Caitlin M. Tressler and Neal J. Zondlo; J. Org. Chem. 2014; 79: 5880−5886; DOI: org/10.1021/jo5008674
γ-(S)-Trifluoromethyl proline: evaluation as a structural substitute of proline for solid state 19F-NMR peptide studies; Vladimir Kubyshkin, Sergii Afonin, Sezgin Kara, Nediljko Budisa, Pavel K. Mykhailiuk, Anne S. Ulrich; Org. Biomol. Chem. 2015; 13: 3171-3181; DOI: 10.1039/c5ob00034c.
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