Journal article
3-fluoroazetidinecarboxylic acids and trans,trans-3,4-difluoroproline as peptide scaffolds: inhibition of pancreatic cancer cell growth by a fluoroazetidine iminosugar
- Abstract:
-
Reverse aldol opening renders amides of 3-hydroxyazetidinecarboxylic acids (3-OH-Aze) unstable above pH 8. Aze, found in sugar beet, is mis-incorporated for proline in peptides in humans and is associated with multiple sclerosis and teratogenesis. Aze-containing peptides may be oxygenated by prolyl hydroxylases resulting in potential damage of the protein by a reverse aldol of the hydroxyazetidine; this, rather than changes in conformation, may account for the deleterious effects of Aze. This...
Expand abstract
- Publication status:
- Published
- Peer review status:
- Peer reviewed
Actions
Access Document
- Files:
-
-
(Preview, pdf, 715.9KB, Terms of use)
-
- Publisher copy:
- 10.1021/acs.joc.5b00463
Authors
Funding
Bibliographic Details
- Publisher:
- American Chemical Society
- Journal:
- Journal of organic chemistry More from this journal
- Volume:
- 80
- Issue:
- 9
- Pages:
- 4244-4258
- Publication date:
- 2015-05-01
- DOI:
- EISSN:
-
1520-6904
- ISSN:
-
0022-3263
Item Description
- Language:
-
English
- Pubs id:
-
pubs:518427
- UUID:
-
uuid:b8edafc6-a1f8-4813-a5af-c59ecdcf24af
- Local pid:
-
pubs:518427
- Source identifiers:
-
518427
- Deposit date:
-
2015-07-14
Terms of use
- Copyright holder:
- American Chemical Society
- Copyright date:
- 2015
- Notes:
- Copyright © 2015 American Chemical Society. This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
Metrics
If you are the owner of this record, you can report an update to it here: Report update to this record