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Stereoselective synthesis of photoreactive peptidomimetic gamma-secretase inhibitors.

The first asymmetric synthesis of novel, potent photoreactive gamma-secretase inhibitors 2 and 3 has been accomplished. Two stereoselective methods for the preparation of lactone 9 are described. Protected benzophenone intermediate 19 is prepared via an aldol-elimination reaction followed by a PtO(2... Full description

Journal Title: The Journal of organic chemistry October 15, 2004, Vol.69(21), pp.7344-7347
Main Author: Chun, Jiong
Other Authors: Yin, Ye Ingrid , Yang, Guangli , Tarassishin, Leonid , Li, Yue-Ming
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 0022-3263
Link: http://search.proquest.com/docview/66954597/?pq-origsite=primo
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recordid: proquest66954597
title: Stereoselective synthesis of photoreactive peptidomimetic gamma-secretase inhibitors.
format: Article
creator:
  • Chun, Jiong
  • Yin, Ye Ingrid
  • Yang, Guangli
  • Tarassishin, Leonid
  • Li, Yue-Ming
subjects:
  • Alzheimer Disease–Enzymology
  • Amyloid Precursor Protein Secretases–Chemistry
  • Aspartic Acid Endopeptidases–Pharmacology
  • Carbamates–Chemistry
  • Cell Membrane–Enzymology
  • Dipeptides–Chemistry
  • Endopeptidases–Pharmacology
  • Enzyme Inhibitors–Chemistry
  • Humans–Drug Effects
  • Molecular Conformation–Chemical Synthesis
  • Molecular Mimicry–Pharmacology
  • Peptide Fragments–Chemistry
  • Photochemistry–Chemistry
  • Stereoisomerism–Chemistry
  • Carbamates
  • Dipeptides
  • Enzyme Inhibitors
  • L 685458
  • Peptide Fragments
  • Amyloid Precursor Protein Secretases
ispartof: The Journal of organic chemistry, October 15, 2004, Vol.69(21), pp.7344-7347
description: The first asymmetric synthesis of novel, potent photoreactive gamma-secretase inhibitors 2 and 3 has been accomplished. Two stereoselective methods for the preparation of lactone 9 are described. Protected benzophenone intermediate 19 is prepared via an aldol-elimination reaction followed by a PtO(2)-catalyzed asymmetric hydrogenation. Two routes leading from 19 to compounds 2 and 3 are evaluated. The application of 3 as an activity-based probe has been demonstrated by localizing gamma-secretase activity in the plasma membrane of intact cells.
language: eng
source:
identifier: ISSN: 0022-3263
fulltext: fulltext
issn:
  • 00223263
  • 0022-3263
url: Link


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titleStereoselective synthesis of photoreactive peptidomimetic gamma-secretase inhibitors.
creatorChun, Jiong ; Yin, Ye Ingrid ; Yang, Guangli ; Tarassishin, Leonid ; Li, Yue-Ming
contributorChun, Jiong (correspondence author) ; Chun, Jiong (record owner)
ispartofThe Journal of organic chemistry, October 15, 2004, Vol.69(21), pp.7344-7347
identifierISSN: 0022-3263
subjectAlzheimer Disease–Enzymology ; Amyloid Precursor Protein Secretases–Chemistry ; Aspartic Acid Endopeptidases–Pharmacology ; Carbamates–Chemistry ; Cell Membrane–Enzymology ; Dipeptides–Chemistry ; Endopeptidases–Pharmacology ; Enzyme Inhibitors–Chemistry ; Humans–Drug Effects ; Molecular Conformation–Chemical Synthesis ; Molecular Mimicry–Pharmacology ; Peptide Fragments–Chemistry ; Photochemistry–Chemistry ; Stereoisomerism–Chemistry ; Carbamates ; Dipeptides ; Enzyme Inhibitors ; L 685458 ; Peptide Fragments ; Amyloid Precursor Protein Secretases
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descriptionThe first asymmetric synthesis of novel, potent photoreactive gamma-secretase inhibitors 2 and 3 has been accomplished. Two stereoselective methods for the preparation of lactone 9 are described. Protected benzophenone intermediate 19 is prepared via an aldol-elimination reaction followed by a PtO(2)-catalyzed asymmetric hydrogenation. Two routes leading from 19 to compounds 2 and 3 are evaluated. The application of 3 as an activity-based probe has been demonstrated by localizing gamma-secretase activity in the plasma membrane of intact cells.
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