Selectively Fluorinated Citronellol Analogues Support a Hydrogen Bonding Donor Interaction with the Human OR1A1 Olfactory Receptor

[Image: see text] C-2 fluorinated and methylated stereoisomers of the fragrance citronellol 1 and its oxalate esters were prepared from (R)-pulegone 11 and explored as agonists of the human olfactory receptor OR1A1 and assayed also against site-specific mutants. There were clear isomer preferences a...

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Autores principales: He, Mengfan, Liu, Weihong, Zhang, Chen, Liu, Yingjian, Zhuang, Hanyi, O’Hagan, David
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9237825/
https://www.ncbi.nlm.nih.gov/pubmed/35686936
http://dx.doi.org/10.1021/acs.orglett.2c01635
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author He, Mengfan
Liu, Weihong
Zhang, Chen
Liu, Yingjian
Zhuang, Hanyi
O’Hagan, David
author_facet He, Mengfan
Liu, Weihong
Zhang, Chen
Liu, Yingjian
Zhuang, Hanyi
O’Hagan, David
author_sort He, Mengfan
collection PubMed
description [Image: see text] C-2 fluorinated and methylated stereoisomers of the fragrance citronellol 1 and its oxalate esters were prepared from (R)-pulegone 11 and explored as agonists of the human olfactory receptor OR1A1 and assayed also against site-specific mutants. There were clear isomer preferences and C-2 difluorination as in 18 led to the most active compound suggesting an important hydrogen bond donor role for citronellol 1. C-2 methylation and the corresponding oxalate ester analogues were less active.
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spelling pubmed-92378252022-06-29 Selectively Fluorinated Citronellol Analogues Support a Hydrogen Bonding Donor Interaction with the Human OR1A1 Olfactory Receptor He, Mengfan Liu, Weihong Zhang, Chen Liu, Yingjian Zhuang, Hanyi O’Hagan, David Org Lett [Image: see text] C-2 fluorinated and methylated stereoisomers of the fragrance citronellol 1 and its oxalate esters were prepared from (R)-pulegone 11 and explored as agonists of the human olfactory receptor OR1A1 and assayed also against site-specific mutants. There were clear isomer preferences and C-2 difluorination as in 18 led to the most active compound suggesting an important hydrogen bond donor role for citronellol 1. C-2 methylation and the corresponding oxalate ester analogues were less active. American Chemical Society 2022-06-10 2022-06-24 /pmc/articles/PMC9237825/ /pubmed/35686936 http://dx.doi.org/10.1021/acs.orglett.2c01635 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle He, Mengfan
Liu, Weihong
Zhang, Chen
Liu, Yingjian
Zhuang, Hanyi
O’Hagan, David
Selectively Fluorinated Citronellol Analogues Support a Hydrogen Bonding Donor Interaction with the Human OR1A1 Olfactory Receptor
title Selectively Fluorinated Citronellol Analogues Support a Hydrogen Bonding Donor Interaction with the Human OR1A1 Olfactory Receptor
title_full Selectively Fluorinated Citronellol Analogues Support a Hydrogen Bonding Donor Interaction with the Human OR1A1 Olfactory Receptor
title_fullStr Selectively Fluorinated Citronellol Analogues Support a Hydrogen Bonding Donor Interaction with the Human OR1A1 Olfactory Receptor
title_full_unstemmed Selectively Fluorinated Citronellol Analogues Support a Hydrogen Bonding Donor Interaction with the Human OR1A1 Olfactory Receptor
title_short Selectively Fluorinated Citronellol Analogues Support a Hydrogen Bonding Donor Interaction with the Human OR1A1 Olfactory Receptor
title_sort selectively fluorinated citronellol analogues support a hydrogen bonding donor interaction with the human or1a1 olfactory receptor
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9237825/
https://www.ncbi.nlm.nih.gov/pubmed/35686936
http://dx.doi.org/10.1021/acs.orglett.2c01635
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