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Screening of chiral shift reagents suitable to generically separate the enantiomers of V-agents by 31P-NMR spectroscopy.

Abstract：

:Fourteen amino acids protected at the N-terminal and at their side chains were screened for resolving the enantiomers of V-agents by NMR. While none of the shift reagents tested showed really effective separation in proton NMR, two of them (BOC-Gln(Xan)-OH, 16, and Z-Arg(Z)2-OH), 21, with 16 superior to 21) were found suitable to separate the enantiomers of all V-agent homologues involved in the test by 31P-NMR. Molar ratios investigated were 1:0.5, 1:1, 1:1.5, 1:2, and 1:3 with the V-agent set to 1 throughout the experiments. All these ratios were more or less effective, but 1:3 was found to separate the V-agents the most reliable way. It is postulated that three chiral solvating molecules are then coordinated around the organophosphate: ion pair formation with the amino nitrogen of the V agent side chain, hydrogen bonding provided by the PO unit, and extension of coordination at the phosphorus atom itself. After chiral separation of VX by semi-preparative LC-MS the enantiomers were examined with both configurations of 16 releasing four different 31P NMR peaks which correspond to four different complexes: R-S3, R-R3, S-R3, and S-S3. Comparing these results with literature data it is assumed that (+)-VX corresponds to the RP configuration and (-)-VX to the SP-configuration.

journal_name

Toxicol Lett

journal_title

Toxicology letters

authors

Koller M,Thiermann H,Worek F

doi

10.1016/j.toxlet.2019.12.004

subject

Has Abstract

pub_date

2020-03-01 00:00:00

pages

28-36

eissn

0378-4274

issn

1879-3169

pii

S0378-4274(19)30389-3

journal_volume

320

pub_type

杂志文章

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