Premium
Stereoselectivity in the Oligomerization of Racemic Tryptophan N ‐Carboxyanhydride (NCA‐Trp) as Determined by Isotope Labeling and Mass Spectrometry
Author(s) -
Blocher Markus,
Hitz Thomas,
Luisi Pier Luigi
Publication year - 2001
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 - 10.1002/1522-2675(20010418)84:4<842::aid-hlca842>3.0.co;2-1
Subject(s) - chemistry , popc , oligomer , stereoselectivity , enantiomer , mass spectrometry , isotopic labeling , isotope , liposome , chromatography , stereochemistry , organic chemistry , bilayer , membrane , biochemistry , physics , quantum mechanics , catalysis
The polycondensation of tryptophan N ‐carboxyanhydride (NCA‐Trp) is investigated in the presence and in the absence of POPC (1‐ O ‐palmitoyl‐2‐ O ‐oleoyl‐ sn ‐glycerol‐3‐ O ‐phosphocholine) liposomes with the aim to study and to quantify possible stereoselective effects of the process. A novel technique, based on isotope labeling of one enantiomer, and high performance liquid chromatography mass spectrometry (LC‐MS) allow determination of the individual stereoisomer distribution of oligomers up to n =10. For the first time, the preferential homochiral growth and the relative stereoisomer distributions for each oligomer length are directly demonstrated.