Rapid Synthesis of Boc-2′,6′-dimethyl-l -tyrosine and Derivatives and Incorporation into Opioid Peptidomimetics
A. Bender
1
,
Nicholas W. Griggs
2
,
Chao Gao
2
,
Tyler J Trask
2
,
John R. Traynor
2
,
H.I. Mosberg
1, 3
Publication type: Journal Article
Publication date: 2015-10-21
scimago Q1
wos Q2
SJR: 0.805
CiteScore: 5.8
Impact factor: 4.0
ISSN: 19485875
PubMed ID:
26713104
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
The unnatural amino acid 2',6'-dimethyl-l-tyrosine has found widespread use in the development of synthetic opioid ligands. Opioids featuring this residue at the N-terminus often display superior potency at one or more of the opioid receptor types, but the availability of the compound is hampered by its cost and difficult synthesis. We report here a short, three-step synthesis of Boc-2',6'-dimethyl-l-tyrosine (3a) utilizing a microwave-assisted Negishi coupling for the key carbon-carbon bond forming step, and employ this chemistry for the expedient synthesis of other unnatural tyrosine derivatives. Three of these derivatives (3c, 3d, 3f) have not previously been examined as Tyr(1) replacements in opioid ligands. We describe the incorporation of these tyrosine derivatives in a series of opioid peptidomimetics employing our previously reported tetrahydroquinoline (THQ) scaffold, and the binding and relative efficacy of each of the analogues at the three opioid receptor subtypes: mu (MOR), delta (DOR), and kappa (KOR).
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19
Total citations:
19
Citations from 2024:
2
(10.53%)
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GOST
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Bender A. et al. Rapid Synthesis of Boc-2′,6′-dimethyl-l-tyrosine and Derivatives and Incorporation into Opioid Peptidomimetics // ACS Medicinal Chemistry Letters. 2015. Vol. 6. No. 12. pp. 1199-1203.
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Bender A., Griggs N. W., Gao C., Trask T. J., Traynor J. R., Mosberg H. Rapid Synthesis of Boc-2′,6′-dimethyl-l-tyrosine and Derivatives and Incorporation into Opioid Peptidomimetics // ACS Medicinal Chemistry Letters. 2015. Vol. 6. No. 12. pp. 1199-1203.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acsmedchemlett.5b00344
UR - https://doi.org/10.1021/acsmedchemlett.5b00344
TI - Rapid Synthesis of Boc-2′,6′-dimethyl-l-tyrosine and Derivatives and Incorporation into Opioid Peptidomimetics
T2 - ACS Medicinal Chemistry Letters
AU - Bender, A.
AU - Griggs, Nicholas W.
AU - Gao, Chao
AU - Trask, Tyler J
AU - Traynor, John R.
AU - Mosberg, H.I.
PY - 2015
DA - 2015/10/21
PB - American Chemical Society (ACS)
SP - 1199-1203
IS - 12
VL - 6
PMID - 26713104
SN - 1948-5875
ER -
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BibTex (up to 50 authors)
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@article{2015_Bender,
author = {A. Bender and Nicholas W. Griggs and Chao Gao and Tyler J Trask and John R. Traynor and H.I. Mosberg},
title = {Rapid Synthesis of Boc-2′,6′-dimethyl-l-tyrosine and Derivatives and Incorporation into Opioid Peptidomimetics},
journal = {ACS Medicinal Chemistry Letters},
year = {2015},
volume = {6},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://doi.org/10.1021/acsmedchemlett.5b00344},
number = {12},
pages = {1199--1203},
doi = {10.1021/acsmedchemlett.5b00344}
}
Cite this
MLA
Copy
Bender, A., et al. “Rapid Synthesis of Boc-2′,6′-dimethyl-l-tyrosine and Derivatives and Incorporation into Opioid Peptidomimetics.” ACS Medicinal Chemistry Letters, vol. 6, no. 12, Oct. 2015, pp. 1199-1203. https://doi.org/10.1021/acsmedchemlett.5b00344.