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Diastereo- And Enantioseparation of a N(α)-Boc Amino Acid With a Zwitterionic Quinine-Based Stationary Phase: Focus on the Stereorecognition Mechanism

Diastereo- And Enantioseparation of a N(α)-Boc Amino Acid With a Zwitterionic Quinine-Based Stationary Phase: Focus on the Stereorecognition Mechanism

Federica Ianni, Andrea Carotti, Maura Marinozzi, Gloria Marcelli, Alessandro Di Michele, Roccaldo Sardella, Wolfgang Lindner, Benedetto Natalini

Anal Chim Acta. 2015 Jul 23;885:174-82.

PMID: 26231903

Abstract:

A chiral chromatography method enabling the simultaneous diastereo- and enantioseparation of N(α)-Boc-N(4)-(hydroorotyl)-4-aminophenylalanine [Boc-Aph(Hor)-OH, 1] was optimized with a quinine-based zwitterionic stationary phase. The polar-ionic eluent system consisting of ACN:MeOH:water-49.7:49.7:0.6 (v/v/v) with formic acid (4.0mM) and diethylamine (2.5mM), allowed the successful separation of the four acid stereoisomers: αd,d-/d,l-1=1.08; αd,l-/l,d-1=1.08; αl,d-/l,l-1=1.40. According to the in-house developed synthetic procedure and the recorded electronic circular dichroism spectra, the following stereoisomeric elution order was readily established in the optimal chromatographic conditions: d,d-1

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
LS7931247	N-(Boc)-6-fluoroindole-2-boronic acid			Price

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