S-Mg₂(dobpdc): a metal–organic framework for determining chirality in amino acids

Abstract

Chirality is a key aspect of amino acids and essential for life. Here, a chiral metal-organic framework, S-Mg2dobpdc, is used to determine the chirality of three BOC protected amino acids...

Amine‐Tagged Fragmented Ligand Installation for Covalent Modification of MOF‐74

“…Although there are no reports of the covalent modification of DOBPDC in Ni 2 (DOBPDC), an extended analogue of MOF‐74, which has larger pores than MOF‐74, can provide a more efficient diffusion of a substrate or diffuse a larger substrate into its framework than MOF‐74 [14, 26–28] . The same synthetic procedure was applied for the synthesis of DEMOF‐II to determine whether the synthetic strategy was valid for the MOF‐74 analogue.…”

Chiral Detection with Coordination Polymers

“…39 QR = 3.12 [40] [ [44] iPr-Chir-UMCM-1 NMR TFPE � 0.4 ppm difference [45] DUT-32-NHProBoc NMR TFPE � 0.6 ppm difference [46] Mg 2 (dobpdc) NMR trans-1,2-diaminocyclohexane 3 ppm difference [47] S-Mg 2 (dobpdc) NMR BOC-alanine BOC-valine BOC-proline Alanine Valine Proline � 1.3 ppm difference [48] [a] Enantioselectivity factors are cited based on ratios given in the literature (e. g. separation factors, quenching ratios, etc. ).…”

“…In a combination of the techniques from the previous two studies, our group grafted a series of BOC-protected amino acids (alanine, valine and proline) onto S-Mg 2 (dobpdc). [48] By observing the 13 C CP MAS NMR signals for specific carbon atoms in the dobpdc 4À ligand, the D/L-enantiomers of each BOC amino acid derivative could be distinguished. Chemical shift differences up to 0.6 ppm were observed between enantiomers, with the largest difference obtained for BOC-alanine (Figure 6).…”

“…Adapted with permission from the Royal Society of Chemistry. [48] restricted to a handful of amino acid and TFPE derivatives, yielding small chemical shift differences. [49] It is only in the last few years that these values have been extended beyond 1.0 ppm, but this increase in enantioselectivity gives hope for the future of the sensing field's applicability.…”

“… 13 C CP MAS NMR spectra of S ‐Mg 2 (dobpdc) appended with BOC‐L‐alanine (black), BOC‐D‐alanine (red), and BOC‐DL‐alanine (blue), showing (a) the full spectrum, (b) magnified section between 145–105 ppm, and (c) magnified section between 60–10 ppm. Adapted with permission from the Royal Society of Chemistry [48] …”