volume 41 issue 31 pages 5795-5798

Protection of 3,4-dihydroxyphenylalanine (DOPA) for Fmoc solid-phase peptide synthesis

Publication typeJournal Article
Publication date2000-07-01
scimago Q3
wos Q3
SJR0.334
CiteScore3.2
Impact factor1.5
ISSN00404039, 18733581
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
Cyclic ethyl orthoformate (Ceof) was utilized as a protecting group to protect the catechol hydroxyl groups of 3,4-dihydroxyphenylalanine (DOPA). This protecting group is stable to strong bases and nucleophiles, and can be removed efficiently by 1 M trimethylsilyl bromide in trifluoroacetic acid in the presence of scavengers at 0°C for 60 min. Fmoc-DOPA(Ceof)-OH was synthesized in high yield and applied along with other Fmoc-amino acids to the solid-phase peptide synthesis of a DOPA-containing decapeptide from a mussel adhesive protein.
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GOST |
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GOST Copy
Hu B., Messersmith P. B. Protection of 3,4-dihydroxyphenylalanine (DOPA) for Fmoc solid-phase peptide synthesis // Tetrahedron Letters. 2000. Vol. 41. No. 31. pp. 5795-5798.
GOST all authors (up to 50) Copy
Hu B., Messersmith P. B. Protection of 3,4-dihydroxyphenylalanine (DOPA) for Fmoc solid-phase peptide synthesis // Tetrahedron Letters. 2000. Vol. 41. No. 31. pp. 5795-5798.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1016/S0040-4039(00)00957-6
UR - https://doi.org/10.1016/S0040-4039(00)00957-6
TI - Protection of 3,4-dihydroxyphenylalanine (DOPA) for Fmoc solid-phase peptide synthesis
T2 - Tetrahedron Letters
AU - Hu, Bi-Huang
AU - Messersmith, Phillip B.
PY - 2000
DA - 2000/07/01
PB - Elsevier
SP - 5795-5798
IS - 31
VL - 41
SN - 0040-4039
SN - 1873-3581
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2000_Hu,
author = {Bi-Huang Hu and Phillip B. Messersmith},
title = {Protection of 3,4-dihydroxyphenylalanine (DOPA) for Fmoc solid-phase peptide synthesis},
journal = {Tetrahedron Letters},
year = {2000},
volume = {41},
publisher = {Elsevier},
month = {jul},
url = {https://doi.org/10.1016/S0040-4039(00)00957-6},
number = {31},
pages = {5795--5798},
doi = {10.1016/S0040-4039(00)00957-6}
}
MLA
Cite this
MLA Copy
Hu, Bi-Huang, and Phillip B. Messersmith. “Protection of 3,4-dihydroxyphenylalanine (DOPA) for Fmoc solid-phase peptide synthesis.” Tetrahedron Letters, vol. 41, no. 31, Jul. 2000, pp. 5795-5798. https://doi.org/10.1016/S0040-4039(00)00957-6.