Synthesis of (+)‐N‐(6‐Ethoxy[2,4‐<sup>3</sup>H]phenyl)‐N‐(1,2,2‐trimethylpropyl)‐2‐nitroethene‐1,1‐diamine ([<sup>3</sup>H]BAY x 9228)

Pleiß, U.; Lenfers, J. B.; Schmitt, P.

doi:10.1002/jlcr.2580330802

Cited by 2 publications

(1 citation statement)

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“…Various experimental conditions including reaction time, hydrogen gas pressure, catalyst type, amount of catalyst and concentration of acid acceptor can affect the selectivity of the hydrogenation. Indeed, several Pd catalyst systems have been described that selectively reduce aryl bromines in the presence of aromatic carbonyl groups and olefins (46–49). The small quantity of Br 2 Bpa‐containing peptides prepared in this study prevented systematic evaluation of these conditions.…”

Section: Discussionmentioning

confidence: 99%

Tritiated photoactivatable analogs of the native human thrombin receptor (PAR‐1) agonist peptide, SFLLRN‐NH₂

Elliott

Hoekstra²,

Derian³

et al. 2001

The Journal of Peptide Research

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Six photoactivatable analogs of the human thrombin receptor activating peptide (TRAP), SFLLRN-NH2, were synthesized by substituting the photoactive amino acid, p-benzoylphenylalanine (Bpa), into each position of the peptide sequence. Platelet aggregation assays indicated that the peptides with Bpa substitutions at positions 3 to 6 retained agonist activity. These peptides were prepared in tritiated form as potential thrombin receptor photoaffinity labels. The [3H]Bpa-containing analogs were constructed by resynthesizing the peptides with the amino acid, 4-benzoyl-2',5'-dibromophenylalanine (Br2Bpa), and subjecting the purified peptides to Pd-catalyzed tritiodebromination. The radiochemical yields for the reductive tritiation were < 2% for peptides with [3H]Bpa in the third and fourth positions, and between 7 and 16% for the peptides with substitutions at the fifth and sixth positions. The low yields were due to over-reduction of the Bpa carbonyl group and nonspecific degradation during reductive tritiation. This report describes the first use of Br2Bpa for the preparation of tritiated photoactivatable peptides.

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Section: Discussionmentioning

confidence: 99%

Tritiated photoactivatable analogs of the native human thrombin receptor (PAR‐1) agonist peptide, SFLLRN‐NH₂

Elliott

Hoekstra²,

Derian³

et al. 2001

The Journal of Peptide Research

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Syntheses and Uses of Isotopically Labelled Compounds ContainingCC,COorCNGroups

Zieliński

Kańska

2009

Patai's Chemistry of Functional Groups

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Introduction Syntheses and Uses of Compounds Containing C  C , C  O or C  N Groups Labelled with Stable Isotopes Synthesis and Uses of Compounds Containing C  C , C  O or CN Groups Labelled with Tritium Syntheses and Uses of Compounds Containing C  C , C  O or CN Groups Labelled with Radioactive Carbon Syntheses and Uses of Compounds Containing C  C , C  O or CN Groups Labelled with Radioactive Halogen Synthesis and Uses of Compounds Containing C  C , C  O , or CN Groups Labelled with Radioactive Sulphur Isotope Effect Studies Acknowledgements

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Synthesis of (+)‐N‐(6‐Ethoxy[2,4‐³H]phenyl)‐N‐(1,2,2‐trimethylpropyl)‐2‐nitroethene‐1,1‐diamine ([³H]BAY x 9228)

Cited by 2 publications

References 5 publications

Tritiated photoactivatable analogs of the native human thrombin receptor (PAR‐1) agonist peptide, SFLLRN‐NH₂

Tritiated photoactivatable analogs of the native human thrombin receptor (PAR‐1) agonist peptide, SFLLRN‐NH₂

Syntheses and Uses of Isotopically Labelled Compounds ContainingCC,COorCNGroups

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Synthesis of (+)‐N‐(6‐Ethoxy[2,4‐3H]phenyl)‐N‐(1,2,2‐trimethylpropyl)‐2‐nitroethene‐1,1‐diamine ([3H]BAY x 9228)

Cited by 2 publications

References 5 publications

Tritiated photoactivatable analogs of the native human thrombin receptor (PAR‐1) agonist peptide, SFLLRN‐NH2

Tritiated photoactivatable analogs of the native human thrombin receptor (PAR‐1) agonist peptide, SFLLRN‐NH2

Syntheses and Uses of Isotopically Labelled Compounds ContainingCC,COorCNGroups

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Product

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Synthesis of (+)‐N‐(6‐Ethoxy[2,4‐³H]phenyl)‐N‐(1,2,2‐trimethylpropyl)‐2‐nitroethene‐1,1‐diamine ([³H]BAY x 9228)

Tritiated photoactivatable analogs of the native human thrombin receptor (PAR‐1) agonist peptide, SFLLRN‐NH₂

Tritiated photoactivatable analogs of the native human thrombin receptor (PAR‐1) agonist peptide, SFLLRN‐NH₂