Synthesis and <sup>13</sup>C NMR Equilibria Studies of (1-<sup>13</sup>C)Leupeptin and Analogs

McConnell, Rose M.; Patterson-Goss, Crissy; Godwin, Walter E.; Stanley, Brant

doi:10.1021/jo980070c

Cited by 2 publications

(2 citation statements)

References 23 publications

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“…These signals also appear in the reaction of [1-13 C]acetaldehyde and polylysine alone. In comparison to other results, these signals at 69.1 and 71.3 ppm are consistent with the formation of stable carbinolamine adducts at the N terminus and -amino groups of polylysine (14). Interestingly enough, when the MDA is in a similar molar ratio with respect to acetaldehyde (Figure 4), the carbinolamine is quite prominent.…”

Section: Resultssupporting

confidence: 89%

Observation of a New Nonfluorescent Malondialdehyde−Acetaldehyde−Protein Adduct by ¹³C NMR Spectroscopy

Kearley

Patel

Chien

et al. 1998

Chem. Res. Toxicol.

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It has been shown that malondialdehyde (MDA) and acetaldehyde react with proteins via the epsilon-amino group of a lysine residue to yield hybrid MDA-acetaldehyde (MAA)-protein adducts. The structure of one MAA adduct has been confirmed to be 4-methyl-1, 4-dihydropyridine-3,5-dicarbaldehyde (3). In this study, 13C NMR spectroscopy was used to identify the structure of a second MAA adduct as 2-formyl-3-(alkylamino)butanal (4). Isotopically labeled [1-13C]acetaldehyde was reacted with MDA and the protein, bovine serum albumin, under a variety of conditions, and the reactions were monitored at various time intervals by 13C NMR. In each experiment, new signals grew in at 50 and 22 ppm. By comparison to model compounds, the signals at 50 ppm correspond to a 2-formyl-3-(alkylamino)butanal adduct and the signals at 22 ppm correspond to the known 1,4-dihydropyridine-3,5-dicarbaldehyde adduct. Similar results were found when the BSA was replaced with polylysine. Overall, it appears that MAA-protein adducts are composed of two major products, 3 and 4.

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Section: Resultssupporting

confidence: 89%

Observation of a New Nonfluorescent Malondialdehyde−Acetaldehyde−Protein Adduct by ¹³C NMR Spectroscopy

Kearley

Patel

Chien

et al. 1998

Chem. Res. Toxicol.

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“…Literature precedents for the synthesis of arginine are rare , and to our knowledge there are no reports of the preparation of l -arginine selectively labeled at C-2. Valuable approaches to unlabeled arginine include the use of aspartic acid and 4-guanidinobutanoic acid as starting materials, but these routes are not readily adapted for the incorporation of carbon-13 at C-2 . Thus we designed an enantioselective approach to Fmoc-Pbf-[2- 13 C]- l -arginine 1 from commercially available [2- 13 C]bromoacetic acid 2 using Williams’ oxazinone as a chiral glycinate equivalent to generate the required stereogenic center.…”

Section: Resultsmentioning

confidence: 99%

Enantioselective Syntheses of α-Fmoc-Pbf-[2-¹³C]-l-arginine and Fmoc-[1,3-¹³C₂]-l-proline and Incorporation into the Neurotensin Receptor 1 Ligand, NT₈₋₁₃

et al. 2009

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Enantioselective syntheses of selectively labeled, orthogonally protected [2-(13)C]-L-arginine and [1,3-(13)C(2)]-L-proline are described from the commercially available precursors [2-(13)C]bromoacetic acid and potassium [(13)C]cyanide. Interestingly the enhanced signal assigned to C-2 in the (13)C NMR spectrum of alpha-Fmoc-Pbf-[2-(13)C]-L-arginine was very broad at room temperature. The two Fmoc-labeled amino acids were used to prepare [2-(13)C]-Arg9 and [1,3-(13)C(2)]-Pro10 labeled ligand (NT(8-13)) by manual Fmoc-SPSS.

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Synthesis and ¹³C NMR Equilibria Studies of (1-¹³C)Leupeptin and Analogs

Cited by 2 publications

References 23 publications

Observation of a New Nonfluorescent Malondialdehyde−Acetaldehyde−Protein Adduct by ¹³C NMR Spectroscopy

Observation of a New Nonfluorescent Malondialdehyde−Acetaldehyde−Protein Adduct by ¹³C NMR Spectroscopy

Enantioselective Syntheses of α-Fmoc-Pbf-[2-¹³C]-l-arginine and Fmoc-[1,3-¹³C₂]-l-proline and Incorporation into the Neurotensin Receptor 1 Ligand, NT₈₋₁₃

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Synthesis and 13C NMR Equilibria Studies of (1-13C)Leupeptin and Analogs

Cited by 2 publications

References 23 publications

Observation of a New Nonfluorescent Malondialdehyde−Acetaldehyde−Protein Adduct by 13C NMR Spectroscopy

Observation of a New Nonfluorescent Malondialdehyde−Acetaldehyde−Protein Adduct by 13C NMR Spectroscopy

Enantioselective Syntheses of α-Fmoc-Pbf-[2-13C]-l-arginine and Fmoc-[1,3-13C2]-l-proline and Incorporation into the Neurotensin Receptor 1 Ligand, NT8−13

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Synthesis and ¹³C NMR Equilibria Studies of (1-¹³C)Leupeptin and Analogs

Observation of a New Nonfluorescent Malondialdehyde−Acetaldehyde−Protein Adduct by ¹³C NMR Spectroscopy

Observation of a New Nonfluorescent Malondialdehyde−Acetaldehyde−Protein Adduct by ¹³C NMR Spectroscopy

Enantioselective Syntheses of α-Fmoc-Pbf-[2-¹³C]-l-arginine and Fmoc-[1,3-¹³C₂]-l-proline and Incorporation into the Neurotensin Receptor 1 Ligand, NT₈₋₁₃