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Solubilization of Peptides in Non‐polar Organic Solvents by the Addition of Inorganic Salts: Facts and Implications
Author(s) -
Seebach Dieter,
Thaler Adrian,
Beck Albert K.
Publication year - 1989
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19890720502
Subject(s) - chemistry , solubility , salt (chemistry) , peptide , stereocenter , polar , solubilization , ether , homogeneous , aqueous solution , inorganic chemistry , stereochemistry , organic chemistry , catalysis , biochemistry , physics , astronomy , thermodynamics , enantioselective synthesis
The solubility of open‐chain peptide derivatives (12 examples) in non‐polar, ether‐type organic solvents may be greatly increased by addition of salts (LiCl, LiBr, LiI, LiBF 4 , LiClO 4 , NaI, MgBr 2 CaBr 2 , ZnCl 2 ) or of titanates (Ti(OEt) 4 , Ti(OCHMe 2 ) 4 ). Examples are reported ( Tables 2–6 ) in which this solubilizing effect leads to peptide concentrations more than one‐hundred‐fold those in the absence of salt ( cf , BocAlaGlyGlyGlyOH in THF from 2g·1 −1 to ≥ 300 g·1 −1 with 6 equiv. of LiCl), 1 H‐NMR Spectra of one of these solutions are reported ( Fig. 1 ). There are no indications for epimerizations of stereogenic centres on the peptide backbone. Possible applications of these solutions in peptide chemistry are discussed.