Bifunctional Chiral Dehydroalanines for Peptide Coupling and Stereoselective S-Michael Addition
Тип публикации: Journal Article
Дата публикации: 2016-06-01
scimago Q1
wos Q1
БС1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5
ISSN: 15237060, 15237052
PubMed ID:
27246362
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Краткое описание
A second generation of chiral bicyclic dehydroalanines easily accessible from serine has been developed. These scaffolds behaved as excellent S-Michael acceptors when tri-O-acetyl-2-acetamido-2-deoxy-1-thio-α-d-galactopyranose (abbreviated as GalNAc-α-SH) was used as a nucleophile. This addition proceeds with total chemo- and stereoselectivity, complete atom economy, quickly, and at room temperature, making it a true click reaction. The Michael adducts were easily transformed into S-(2-acetamido-2-deoxy-α-d-galactopyranosyl)-l- and -d-cysteines, which can be regarded as mimics of the Tn antigen derived from l-Ser (α-d-GalNAc-l-Ser) and d-Ser (α-d-GalNAc-d-Ser), respectively.
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Gutiérrez Jiménez M. I. et al. Bifunctional Chiral Dehydroalanines for Peptide Coupling and Stereoselective S-Michael Addition // Organic Letters. 2016. Vol. 18. No. 12. pp. 2796-2799.
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Gutiérrez Jiménez M. I., Aydillo C., Navo C. D., Avenoza A., Corzana F., Jiménez-Osés G., Zurbano M. M., Busto J. H., Peregrina J. M. Bifunctional Chiral Dehydroalanines for Peptide Coupling and Stereoselective S-Michael Addition // Organic Letters. 2016. Vol. 18. No. 12. pp. 2796-2799.
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TY - JOUR
DO - 10.1021/acs.orglett.6b00840
UR - https://doi.org/10.1021/acs.orglett.6b00840
TI - Bifunctional Chiral Dehydroalanines for Peptide Coupling and Stereoselective S-Michael Addition
T2 - Organic Letters
AU - Gutiérrez Jiménez, Marta I
AU - Aydillo, Carlos
AU - Navo, Claudio D.
AU - Avenoza, Alberto
AU - Corzana, Francisco
AU - Jiménez-Osés, Gonzalo
AU - Zurbano, María M
AU - Busto, Jesús H.
AU - Peregrina, Jesús M.
PY - 2016
DA - 2016/06/01
PB - American Chemical Society (ACS)
SP - 2796-2799
IS - 12
VL - 18
PMID - 27246362
SN - 1523-7060
SN - 1523-7052
ER -
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BibTex (до 50 авторов)
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@article{2016_Gutiérrez Jiménez,
author = {Marta I Gutiérrez Jiménez and Carlos Aydillo and Claudio D. Navo and Alberto Avenoza and Francisco Corzana and Gonzalo Jiménez-Osés and María M Zurbano and Jesús H. Busto and Jesús M. Peregrina},
title = {Bifunctional Chiral Dehydroalanines for Peptide Coupling and Stereoselective S-Michael Addition},
journal = {Organic Letters},
year = {2016},
volume = {18},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/acs.orglett.6b00840},
number = {12},
pages = {2796--2799},
doi = {10.1021/acs.orglett.6b00840}
}
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MLA
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Gutiérrez Jiménez, Marta I., et al. “Bifunctional Chiral Dehydroalanines for Peptide Coupling and Stereoselective S-Michael Addition.” Organic Letters, vol. 18, no. 12, Jun. 2016, pp. 2796-2799. https://doi.org/10.1021/acs.orglett.6b00840.