Facile access to unnatural dipeptide-alcohols based on cis-2,5-disubstituted pyrrolidines

Well-defined unnatural dipeptide-alcohols based on a cis-2,5-disubstitued pyrrolidine backbone were synthesized from commercially available starting materials meso-diethyl-2,5-dibromoadipate, (S)-(-)-1-phenylethylamine, and phenylalaninol. The structures of these unnatural dipeptide-alcohols are sup...

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Veröffentlicht in:	Molecules (Basel, Switzerland) Switzerland), 2015-02, Vol.20 (2), p.2922-2930
Hauptverfasser:	Jia, Yan-Yan, Li, Xiao-Ye, Wang, Ping-An, Wen, Ai-Dong
Format:	Artikel
Sprache:	eng
Schlagworte:	Adipates - chemistry Alcohol Alcohols - chemical synthesis Alcohols - chemistry Amino acids Chromatography cis-2,5-disubstituted pyrrolidine Crystallography, X-Ray Dipeptides - chemical synthesis Dipeptides - chemistry hydrogenolysis Magnetic Resonance Spectroscopy Molecular Structure Peptides Peptidomimetics Pharmacy Phenethylamines - chemistry Phenylalanine - analogs & derivatives Phenylalanine - chemistry phenylalaninol Pyrrolidines - chemistry Stereoisomerism unnatural dipeptide-alcohol
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Zusammenfassung:	Well-defined unnatural dipeptide-alcohols based on a cis-2,5-disubstitued pyrrolidine backbone were synthesized from commercially available starting materials meso-diethyl-2,5-dibromoadipate, (S)-(-)-1-phenylethylamine, and phenylalaninol. The structures of these unnatural dipeptide-alcohols are supported by HRMS, 1H- and 13C-NMR spectroscopy. These unnatural dipeptide-alcohols can act as building blocks for peptidomimetics.
ISSN:	1420-3049 1420-3049
DOI:	10.3390/molecules20022922