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Dean A Sherry - One of the best experts on this subject based on the ideXlab platform.
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detection of glucose derived d and l lactate in cancer cells by the use of a chiral nmr Shift Reagent
Cancer and Metabolism, 2021Co-Authors: Eul Hyun Suh, Dean A Sherry, Carlos F G C Geraldes, Sara Chirayil, Brandon Faubert, Raul Ayala, Ralph J DeberardinisAbstract:BACKGROUND Excessive lactate production, a hallmark of cancer, is largely formed by the reduction of pyruvate via lactate dehydrogenase (LDH) to L-lactate. Although D-lactate can also be produced from glucose via the methylglyoxal pathway in small amounts, less is known about the amount of D-lactate produced in cancer cells. Since the stereoisomers of lactate cannot be distinguished by conventional 1H NMR spectroscopy, a chiral NMR Shift Reagent was used to fully resolve the 1H NMR resonances of D- and L-lactate. METHODS The production of L-lactate from glucose and D-lactate from methylglyoxal was first demonstrated in freshly isolated red blood cells using the chiral NMR Shift Reagent, YbDO3A-trisamide. Then, two different cell lines with high GLO1 expression (H1648 and H 1395) were selected from a panel of over 80 well-characterized human NSCLC cell lines, grown to confluence in standard tissue culture media, washed with phosphate-buffered saline, and exposed to glucose in a buffer for 4 h. After 4 h, a small volume of extracellular fluid was collected and mixed with YbDO3A-trisamide for analysis by 1H NMR spectroscopy. RESULTS A suspension of freshly isolated red blood cells exposed to 5mM glucose produced L-lactate as expected but very little D-lactate. To evaluate the utility of the chiral NMR Shift Reagent, methylglyoxal was then added to red cells along with glucose to stimulate the production of D-lactate via the glyoxalate pathway. In this case, both D-lactate and L-lactate were produced and their NMR chemical Shifts assigned. NSCLC cell lines with different expression levels of GLO1 produced both L- and D-lactate after incubation with glucose and glutamine alone. A GLO1-deleted parental cell line (3553T3) showed no production of D-lactate from glucose while re-expression of GLO1 resulted in higher production of D-lactate. CONCLUSIONS The Shift-Reagent-aided NMR technique demonstrates that D-lactate is produced from glucose in NSCLC cells via the methylglyoxal pathway. The biological role of D-lactate is uncertain but a convenient method for monitoring D-lactate production could provide new insights into the biological roles of D- versus L-lactate in cancer metabolism.
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imaging extracellular lactate in vitro and in vivo using cest mri and a paramagnetic Shift Reagent
Chemistry: A European Journal, 2017Co-Authors: Lei Zhang, Piyu Zhao, André F. Martins, Dean A Sherry, Yuyan Mai, Alexander M Funk, Veronica Clavijo Jordan, Shanrong Zhang, Wei ChenAbstract:Overproduction of lactate is a hallmark of cancer, yet a method to quantitatively measure lactate production by cancer cells is not straight-forward. Chemical exchange saturation transfer magnetic resonance imaging (CEST MRI) can potentially be used to image lactate but the small difference in chemical Shift of the lactate -OH proton and water proton resonances make it challenging. Like other spectroscopic methods, CEST MRI cannot discriminate intracellular lactate from extracellular lactate. Herein, we demonstrate a relatively simple way to Shift the lactate -OH proton resonance far away from water by addition of the paramagnetic Shift Reagent, EuDO3A, while retaining the CEST properties of lactate itself. The potential of the method was demonstrated by imaging extracellular lactate excreted from lung cancer cells in tissue culture without interference from other components in the culture media and by imaging excess lactate excreted into the bladder of a mouse.
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quantitation of intracellular na in vivo by using tmdotp5 as an nmr Shift Reagent and extracellular marker
Journal of Applied Physiology, 1998Co-Authors: Patrick M Winter, Viswanathan Seshan, Janice D Makos, Navin Bansal, Dean A Sherry, Craig R MalloyAbstract:A method is presented to measure the absolute concentration of intracellular Na+([Na+]i) in vivo by using interleaved 23Na- and 31P-nuclear magnetic resonance (NMR) spectroscopy and TmDOTP5− as Shift Reagent and chemical marker of tissue extracellular space (ECS). The technique was used to determine [Na+]iand relative ECS in livers of control rats (21 ± 3 and 0.11 ± 0.02 mM, respectively) and in rats exposed to carbon tetrachloride (103 ± 29 and 0.23 ± 0.03 mM, respectively). The NMR measurements were confirmed independently on excised tissue samples by using atomic absorption spectroscopy. The results confirm that TmDOTP5− can be used as a combined cation Shift Reagent and ECS marker, thereby allowing quantitation of [Na+]iin vivo by NMR.
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ion pairing interactions between co en 3 3 and the 23 na nmr frequency Shift Reagent tmdotp 5
Inorganic Chemistry, 1997Co-Authors: Charles Jr Springer, Dean A SherryAbstract:: Three new formulations of TmDOTP(5)(-) (DOTP(8)(-) = 1,4,7,10-tetraazacyclododecane-1,4,7,11-tetrakis(methylenephosphonate)) have been prepared in an effort to develop a low-osmolality form of the (23)Na frequency Shift Reagent (SR). Equally concentrated (0.32 M) solutions of (MegH)(4)HTmDOTP (Meg = N-methylglucamine or meglumine), Na(4)HTmDOTP, and [Co(en)(3)](4/3)HTmDOTP have solution osmolalities of 1245, 1040, and 707 mOsm/kg, respectively, comparable to the ionic and non-ionic gadolinium-based MRI contrast agent preparations in clinical use. An analysis of (23)Na and (59)Co frequency Shifts induced by TmDOTP(5)(-) indicated that Co(en)(3)(3+) can form both 1:1 and 2:1 adducts with TmDOTP(5)(-) with (log) binding constants of 3.1 +/- 0.4 and 2.5 +/- 0.4, respectively. These values were comparable with those obtained by analysis of the (1)H frequency Shifts observed for Co(en)(3)(3+) upon binding to HoDOTP(5)(-). The (1)H Shifts of Co(en)(3)(3+) signals induced by YbDOTP(5)(-) at pH 7.4 were fitted best by a 1:1 binding model with a conditional binding constant of 3.1 +/- 0.2. The (59)Co and (1)H limiting frequency Shifts of Co(en)(3)(3+) could be fitted with a dipolar Shift model in which the Co atom of the Co(en)(3)(3+) cation is located 5.0 +/- 0.3 A from the Ln atom of the LnDOTP(5)(-) chelate, and with an angle of 40 +/- 0.2 degrees between the Co-Ln vector and the 4-fold symmetry axis of the LnDOTP(5)(-) complex. Ion pairing of Co(en)(3)(3+) and TmDOTP(5)(-) was significant enough in both saline and human blood plasma to reduce the effectiveness of the (23)Na frequency SR. Comparisons between all formulations suggested that Na(4)HTmDOTP represents the best compromise of lower osmolality with minimal reduction of SR Shift potency.
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7li 6li 23na and 133cs multinuclear nmr studies of adducts formed with Shift Reagent tmdotp5
Inorganica Chimica Acta, 1996Co-Authors: Dean A SherryAbstract:Abstract Interactions between Li + , Na + , Cs + , Ca 2+ and Mg 2+ and the Shift Reagent (SR), TmDOTP 5 were studied by 7 Li, 6 Li, 23 Na and 133 Cs multinulear NMR spectroscopy. The unusually large paramagnetic Shifts (⪢100 ppm) observed in the cation NMR resonances at low alkali metal ion to TmDOTP 5− ratios indicated that the cations bind near the 4-fold symmetry axis of the complex. The geometric parameters for the adducts formed between 7 Li, 6 Li, 23 Na and 133 Cs cations and TmDOTP 5− were obtained from Shift and relaxation rate data and compared with those calculated using MMX energy minimization techniques. It is found that the larger Cs + ion lies closest to the 4-fold axis of symmetry and displays the largest binding constant. The smaller Li + ion deviates most from the 4-fold symmetry axis and has a less favorable binding interaction than Cs + . Na + lies somewhere between these two extremes but has the largest limiting Shifts due to its favorable distance from the paramagnetic metal center. A significant reversal of the 23 Na Shift upon addition of Ca 2+ and Mg 2+ indicate that these two divalent cations form very stable 1:1 adducts with TmDOTP 5 (log K (Ca 2+ ) = 5.69 and log Kt (Mg 2+ ) = 3.85). An analysis of the Mg 2+ titration data shows that the 2Mg 2+ :TmDOTP 5− adduct becomes dominant at high Mg 2+ /TmDOTP 5− ratio (log K 2 (Mg 2+ ) = 2.17). The significant influence of NH 4 + on the TmDOTP 5− -induced 6 Li, Shifts suggests that the NH 4 + ion may form multiple H-bonds with the SR along the 4-fold axis of symmetry.
Gabriel A Elgavish - One of the best experts on this subject based on the ideXlab platform.
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the effects of the nmr Shift Reagents dy ppp 2 dy ttha and tm dotp on developed pressure in isolated perfused rat hearts the role of Shift Reagent calcium complexes
Journal of Molecular and Cellular Cardiology, 2001Co-Authors: Balazs Gaszner, Tamas Simor, Gabor Hild, Gabriel A ElgavishAbstract:Abstract The 23 Na NMR Shift-Reagent complexes (Dy(PPP) 2 , Dy(TTHA), and Tm(DOTP)) bind stoichiometric amounts of Ca 2+ . Thus, in perfused rat heart systems, a supplementation of Ca 2+ is required to maintain the requisite extracellular free calcium concentration ([Ca o ] f ) and to approximate a physiological level of contractile function. The amount of Reagent-bound Ca 2+ in a heart perfusate that contains a Shift-Reagent depends on: (1) Ca 2+ binding by excess ligand used during the preparation of the Shift-Reagent; and (2) the Ca 2+ binding affinity of the Shift-Reagent. To address point 1), we introduced a 1 H and 31 P NMR spectroscopic titration method to quantify directly the concentration of the excess ligand. We also used this method to minimize the amount of excess ligand (L) and thus the amount of Ca·L complex. To address point (2), we determined the stepwise K d (μ m ) values of the Ca complexes of the three Shift-Reagents·: Dy(PPP) 2 , K d1 =0.09, K d2 =7.9; Dy(TTHA), K d1 =10.66, K d2 =10.12; and Tm(DOTP), K d1 =0.502, K d2 =4.98. The K d values of the Ca complexes of the phosphonate and triphosphate based Shift-Reagents, Tm(DOTP) and Dy(PPP) 2 , respectively, are lower than those of the polyaminocarboxylate-based Dy(TTHA), indicating stronger Ca binding affinities for the former two types of complexes. We have also shown a positive correlation between [Ca o ] f and left ventricular developed pressure (LVDP) in perfused rat hearts. Dy(TTHA) has shown no effect on LVDP v [Ca o ] f . The LVDP values in the presence of the phosphonate and triphosphate based Shift-Reagents, however, were significantly higher than expected from the [Ca o ] f levels alone. Thus a positive inotropic effect, independent of [Ca o ] f , is evident in the presence of Tm(DOTP) or Dy(PPP) 2 .
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improvement of spectral resolution in Shift Reagent aided 23na nmr spectroscopy in the isolated perfused rat heart system
Magnetic Resonance in Medicine, 1991Co-Authors: Sandra K Miller, Gerald M Pohost, Gabriel A ElgavishAbstract:The level of intracellular sodium (Nai) is maintained at approximately 14 m M in healthy myocytes. When myocytes are damaged, Nai increases and therefore the level of Nai may be a means of evaluating myocardial cell integrity. A particularly useful method to monitor Nai levels is 23Na NMR spectroscopy. However, because of the isochronous nature of the extracellular sodium (Nao) and Nai NMR signals, paramagnetic lanthanide Shift Reagents (LSR), such as dysprosium triphosphate, Dy(PPP)72, have been used to Shift the Nao signal. This reveals the unShifted Nai signal and allows the NMR monitoring of Nai in isolated perfused hearts and other systems. A major shortcoming of this method (the “Shift-only” method) is in the need to minimize the Nao signal by not submerging the perfused hearts in Na+-containing buffer. An equally undesirable alternative is the utilization of relatively high concentrations of LSR to Shift a large Nao signal sufficiently to enable reasonable resolution and quantitation of Nai. We present here a method, the “Shiftrelaxation” method, which is a combination of using a mixture of Dy(PPP)72, a Shift Reagent, and gadolinium triphosphate, Gd(PPP)72, a relaxation agent, with data acquisition using an inversion-recovery (IR) pulse sequence. This combination allows differentiation between Nao and Nai by the difference in their respective T1 values in addition to the Shift between them. With this technique we can selectively minimize the extracellular signal and therefore minimize the need for a large Dy-induced Shift, as well as allow data acquisition on a heart submerged in Na+ -containing perfusate. The resulting improved discrimination between Nai and Nao at relatively low levels of LSR should be helpful for ultimate in vivo application and potential clinical applications, where a lower dose of LSR also means a decreased possibility of physiologically deleterious effects. Also included in this paper is a method for the quick determination of an accurate 180° pulse which is required for the optimization of the IR method. © 1991 Academic Press, Inc.
Navin Bansal - One of the best experts on this subject based on the ideXlab platform.
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tmdotp5 as a 23na Shift Reagent for the subcutaneously implanted 9l gliosarcoma in rats
Magnetic Resonance in Medicine, 2001Co-Authors: Patrick M Winter, Navin BansalAbstract:The use of TmDOTP(5-) as an in vivo (23)Na NMR Shift Reagent (SR) for subcutaneously implanted 9L gliosarcoma was evaluated. TmDOTP(5-) produced a single sharp extracellular peak after about 50-60 min of infusion, and did not cause any changes in the (31)P resonance areas or chemical Shifts, suggesting that the SR is homogeneously distributed in the extracellular space and does not alter tumor bioenergetic status. TmDOTP(5-) and CoEDTA(-) as extracellular space markers gave identical results for relative extracellular space (0.25 +/- 0.03 and 0.25 +/- 0.04, respectively) and intracellular Na(+) concentration (19.3 +/- 4.0 mM and 18.6 +/- 3.9 mM, respectively), indicating that the biodistribution of the SR is the same as the well-accepted extracellular space marker. The in vivo T(1) and T(2) relaxation times of intra- and extracellular Na(+) were also measured. Our results indicate that TmDOTP(5-) promises to be an effective Shift Reagent and extracellular space marker in the 9L gliosarcoma and perhaps other tumors. Magn Reson Med 45:436-442, 2001.
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quantitation of intracellular na in vivo by using tmdotp5 as an nmr Shift Reagent and extracellular marker
Journal of Applied Physiology, 1998Co-Authors: Patrick M Winter, Viswanathan Seshan, Janice D Makos, Navin Bansal, Dean A Sherry, Craig R MalloyAbstract:A method is presented to measure the absolute concentration of intracellular Na+([Na+]i) in vivo by using interleaved 23Na- and 31P-nuclear magnetic resonance (NMR) spectroscopy and TmDOTP5− as Shift Reagent and chemical marker of tissue extracellular space (ECS). The technique was used to determine [Na+]iand relative ECS in livers of control rats (21 ± 3 and 0.11 ± 0.02 mM, respectively) and in rats exposed to carbon tetrachloride (103 ± 29 and 0.23 ± 0.03 mM, respectively). The NMR measurements were confirmed independently on excised tissue samples by using atomic absorption spectroscopy. The results confirm that TmDOTP5− can be used as a combined cation Shift Reagent and ECS marker, thereby allowing quantitation of [Na+]iin vivo by NMR.
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tmdotp5 as a 23na Shift Reagent for the in vivo rat kidney
Magnetic Resonance in Medicine, 1995Co-Authors: Viswanathan Seshan, M J Germann, A D Sherry, P Preisig, C R Malloy, Navin BansalAbstract:Since transmembrane sodium gradient is essential to man cell functions, there is continuing interest in methods tha differentiate intracellular and extracellular Na + . In the kidney, Shift Reagent (SR) aided 23 Na magnetic resonance spectros copy (MRS) has been successfully used only in isolated cells tubules, and the perfused organ. In this report, we demon strate for the first time that TmDOTP 5- can be used to distin guish Na + compartments in kidneys in vivo. Infusion of 80 mM TmDOTP 5- without added Ca 2+ produced three resolved 23 Na resonances, which we have assigned to intracellular Na + , vascular Na + , and intraluminal Na + . In comparison, infusion o 400 mM DyTTHA 3- produced two broad and unresolved resonances. The 31 P spectra of the cellular high energy phosphate metabolites indicate that TmDOTP 5- is safe for in vivo applications. Washout studies suggest that this SR display renal clearance similar to that of MR imaging contrast agents However, the glomerular filtration rate (GFR) in animals in fused with TmDOTP 5- was reduced by 49% compared with the GFR in control animals, perhaps due to the hypotensive effects of the SR. We conclude that TmDOTP 5- is effectively cleared from the blood of live animals but that a different formulation will be required for clinical application.
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thulium 1 4 7 10 tetraazacyclododecane 1 4 7 10 tetrakis methylene phosphonate as a 23na Shift Reagent for the in vivo rat liver
Biochemistry, 1993Co-Authors: Navin Bansal, Viswanathan Seshan, Craig R Malloy, M J Germann, G T Shires, A D SherryAbstract:The use of thulium 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrakis(methylene phosphonate (TmDOTP5-) as an in vivo 23Na NMR Shift Reagent for rat liver was evaluated by collecting interleaved 23Na and 31P spectra. Infusion of 80 mM TmDOTP5- without added Ca2+ produced baseline-resolved peaks from intra- and extracellular sodium without producing any changes in phosphate metabolite resonances or intracellular pH. Several key physiological parameters measured in parallel groups of animals confirmed that liver physiology is largely unaffected by this Shift Reagent. A direct comparison of TmDOTP5- versus DyTTHA3- showed that after infusion of 5-8 times more DyTTHA3-, the extracellular sodium peak Shifted by the same amount as with TmDOTP5-, but the two 23Na resonances were very broad and not resolved. The baseline-resolved peaks with TmDOTP5- allowed us to measure the in vivo T1 and T2 relaxation characteristics of intra- and extracellular Na+. The measured T1, T2s, and T2f values and the relative contributions from the slow and fast T2 components for intracellular Na+ in liver did not differ significantly from the values reported for perfused frog heart. The T1 and T2 relaxation curves of the extracellular Na+ resonances fit a monoexponential function. Analysis of the relative contribution of the fast- and slow-relaxing T2 components from intracellular Na+ resulted in a calculated visibility factor of 69 +/- 4% and the intracellular Na+ concentration calculated from the NMR peak intensity ratio, the measured visibility factor, and literature values of intra- and extracellular volume was 19 mM. These results indicate that TmDOTP5- promises to be quite useful as an in vivo Shift Reagent for liver and other organs.
W. R. Scheidt - One of the best experts on this subject based on the ideXlab platform.
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a cobalt iii chiroporphyrin and its amine adducts a potential chiral nmr Shift Reagent for amines
Inorganic Chemistry, 1998Co-Authors: D Toronto, François Sarrazin, Maoyu Shang, Jacques Pecaut, Jean-claude Marchon, W. R. ScheidtAbstract:The chlorocobalt(III) complex of alphabetaalphabeta-tetramethylchiroporphyrin, CoCl(TMCP), has been prepared as a potential enantioselective host or chiral NMR Shift Reagent for optically active amines. The X-ray structure of CoCl(OHCH(2)CH(3))(TMCP) shows the six-coordinate cobalt(III) ion at the center of a strongly ruffled porphyrin. The 2-fold-disordered ethanol ligand interacts with the chiroporphyrin host by two C-H.O hydrogen bonds to the carbonyl groups of two ester substituents. Primary amines bind to this diamagnetic cobalt(III) center to form cationic 2:1 complexes in which the (1)H NMR resonances of the axial ligands are Shifted upfield of tetramethylsilane by the porphyrin ring current. Coordinated enantiopure 2-alkylamines exhibit NMR signals for the protons of the amine group which are characteristic of their (R or S) absolute configuration. The bis-complexes of the same amines in racemic form exist as three different species, (R,R), (S,S), and (R,S), in 1:1:2 relative ratios. Negligible enantioselection by the chiral host suggests kinetic control of bis(amine) complex formation on cobalt(III). The X-ray structure of the bis((S)-2-butylamine) complex [Co((S)-NH(2)CH(CH(3))CH(2)CH(3))(2)(TMCP)][CoCl(4)](0.5) shows a 2-fold-disordered amine on one face of the porphyrin only. The unique amine on the other face is held within the porphyrin groove by a network of weak interactions including N-H.O and C-H.O hydrogen bonds. With its ability to induce good resolution of axial ligand (1)H NMR resonances and slow dissociation kinetics of its bis-adducts, CoCl(TMCP) may be useful as a chiral NMR Shift Reagent for conformational studies of chiral amines and as an analytical Reagent for the determination of their enantiomer composition.
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a cobalt iii chiroporphyrin and its amine adducts a potential chiral nmr Shift Reagent for amines
Inorganic Chemistry, 1998Co-Authors: D Toronto, François Sarrazin, Maoyu Shang, Jacques Pecaut, Jean-claude Marchon, W. R. ScheidtAbstract:The chlorocobalt(III) complex of αβαβ-tetramethylchiroporphyrin, CoCl(TMCP), has been prepared as a potential enantioselective host or chiral NMR Shift Reagent for optically active amines. The X-ray structure of CoCl(OHCH2CH3)(TMCP) shows the six-coordinate cobalt(III) ion at the center of a strongly ruffled porphyrin. The 2-fold-disordered ethanol ligand interacts with the chiroporphyrin host by two C−H···O hydrogen bonds to the carbonyl groups of two ester substituents. Primary amines bind to this diamagnetic cobalt(III) center to form cationic 2:1 complexes in which the 1H NMR resonances of the axial ligands are Shifted upfield of tetramethylsilane by the porphyrin ring current. Coordinated enantiopure 2-alkylamines exhibit NMR signals for the protons of the amine group which are characteristic of their (R or S) absolute configuration. The bis-complexes of the same amines in racemic form exist as three different species, (R,R), (S,S), and (R,S), in 1:1:2 relative ratios. Negligible enantioselection by ...
D Toronto - One of the best experts on this subject based on the ideXlab platform.
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a cobalt iii chiroporphyrin and its amine adducts a potential chiral nmr Shift Reagent for amines
Inorganic Chemistry, 1998Co-Authors: D Toronto, François Sarrazin, Maoyu Shang, Jacques Pecaut, Jean-claude Marchon, W. R. ScheidtAbstract:The chlorocobalt(III) complex of alphabetaalphabeta-tetramethylchiroporphyrin, CoCl(TMCP), has been prepared as a potential enantioselective host or chiral NMR Shift Reagent for optically active amines. The X-ray structure of CoCl(OHCH(2)CH(3))(TMCP) shows the six-coordinate cobalt(III) ion at the center of a strongly ruffled porphyrin. The 2-fold-disordered ethanol ligand interacts with the chiroporphyrin host by two C-H.O hydrogen bonds to the carbonyl groups of two ester substituents. Primary amines bind to this diamagnetic cobalt(III) center to form cationic 2:1 complexes in which the (1)H NMR resonances of the axial ligands are Shifted upfield of tetramethylsilane by the porphyrin ring current. Coordinated enantiopure 2-alkylamines exhibit NMR signals for the protons of the amine group which are characteristic of their (R or S) absolute configuration. The bis-complexes of the same amines in racemic form exist as three different species, (R,R), (S,S), and (R,S), in 1:1:2 relative ratios. Negligible enantioselection by the chiral host suggests kinetic control of bis(amine) complex formation on cobalt(III). The X-ray structure of the bis((S)-2-butylamine) complex [Co((S)-NH(2)CH(CH(3))CH(2)CH(3))(2)(TMCP)][CoCl(4)](0.5) shows a 2-fold-disordered amine on one face of the porphyrin only. The unique amine on the other face is held within the porphyrin groove by a network of weak interactions including N-H.O and C-H.O hydrogen bonds. With its ability to induce good resolution of axial ligand (1)H NMR resonances and slow dissociation kinetics of its bis-adducts, CoCl(TMCP) may be useful as a chiral NMR Shift Reagent for conformational studies of chiral amines and as an analytical Reagent for the determination of their enantiomer composition.
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a cobalt iii chiroporphyrin and its amine adducts a potential chiral nmr Shift Reagent for amines
Inorganic Chemistry, 1998Co-Authors: D Toronto, François Sarrazin, Maoyu Shang, Jacques Pecaut, Jean-claude Marchon, W. R. ScheidtAbstract:The chlorocobalt(III) complex of αβαβ-tetramethylchiroporphyrin, CoCl(TMCP), has been prepared as a potential enantioselective host or chiral NMR Shift Reagent for optically active amines. The X-ray structure of CoCl(OHCH2CH3)(TMCP) shows the six-coordinate cobalt(III) ion at the center of a strongly ruffled porphyrin. The 2-fold-disordered ethanol ligand interacts with the chiroporphyrin host by two C−H···O hydrogen bonds to the carbonyl groups of two ester substituents. Primary amines bind to this diamagnetic cobalt(III) center to form cationic 2:1 complexes in which the 1H NMR resonances of the axial ligands are Shifted upfield of tetramethylsilane by the porphyrin ring current. Coordinated enantiopure 2-alkylamines exhibit NMR signals for the protons of the amine group which are characteristic of their (R or S) absolute configuration. The bis-complexes of the same amines in racemic form exist as three different species, (R,R), (S,S), and (R,S), in 1:1:2 relative ratios. Negligible enantioselection by ...