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However, a comparison of the hydrophobicity values gained from different techniques, and their relative ranking, is not straightforward, as the interactions between the environment and the amino acid are unique to each method. Here, we overcome this limitation by studying the properties of amino acids in the clean\u2010room environment of the gas phase. In the gas phase, entropic contributions from the hydrophobic effect are by default absent and only the polarity of the side chain dictates the self\u2010assembly. This allows for the derivation of a novel hydrophobicity scale, which is based solely on the interaction between individual amino acid units within the cluster and thus more accurately reflects the intrinsic nature of a side chain. This principle can be further applied to classify non\u2010natural derivatives, as shown here for fluorinated amino acid variants.<\/jats:p>","DOI":"10.1002\/anie.201813954","type":"journal-article","created":{"date-parts":[[2019,4,8]],"date-time":"2019-04-08T12:34:05Z","timestamp":1554726845000},"page":"8216-8220","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":51,"title":["An Intrinsic Hydrophobicity Scale for Amino Acids and Its Application to Fluorinated Compounds"],"prefix":"10.1002","volume":"58","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-6757-3151","authenticated-orcid":false,"given":"Waldemar","family":"Hoffmann","sequence":"first","affiliation":[{"name":"Freie Universit\u00e4t Berlin Department of Biology, Chemistry and Pharmacy  Takustrasse 3\/K\u00f6nigin-Luise-Strasse 2+4 14195 Berlin Germany"},{"name":"Fritz-Haber-Institut der Max-Planck-Gesellschaft Department of Molecular Physics  Faradayweg 4\u20136 14195 Berlin Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jennifer","family":"Langenhan","sequence":"additional","affiliation":[{"name":"Fritz-Haber-Institut der Max-Planck-Gesellschaft Department of Molecular Physics  Faradayweg 4\u20136 14195 Berlin Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5519-3426","authenticated-orcid":false,"given":"Susanne","family":"Huhmann","sequence":"additional","affiliation":[{"name":"Freie Universit\u00e4t Berlin Department of Biology, Chemistry and Pharmacy  Takustrasse 3\/K\u00f6nigin-Luise-Strasse 2+4 14195 Berlin Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Johann","family":"Moschner","sequence":"additional","affiliation":[{"name":"Freie Universit\u00e4t Berlin Department of Biology, Chemistry and Pharmacy  Takustrasse 3\/K\u00f6nigin-Luise-Strasse 2+4 14195 Berlin Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4458-6096","authenticated-orcid":false,"given":"Rayoon","family":"Chang","sequence":"additional","affiliation":[{"name":"Freie Universit\u00e4t Berlin Department of Biology, Chemistry and Pharmacy  Takustrasse 3\/K\u00f6nigin-Luise-Strasse 2+4 14195 Berlin Germany"},{"name":"Fritz-Haber-Institut der Max-Planck-Gesellschaft Department of Molecular Physics  Faradayweg 4\u20136 14195 Berlin Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Matteo","family":"Accorsi","sequence":"additional","affiliation":[{"name":"Freie Universit\u00e4t Berlin Department of Biology, Chemistry and Pharmacy  Takustrasse 3\/K\u00f6nigin-Luise-Strasse 2+4 14195 Berlin Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5844-4585","authenticated-orcid":false,"given":"Jongcheol","family":"Seo","sequence":"additional","affiliation":[{"name":"Fritz-Haber-Institut der Max-Planck-Gesellschaft Department of Molecular Physics  Faradayweg 4\u20136 14195 Berlin Germany"},{"name":"present address: University of Science and Technology (POSTECH) Department of Chemistry  77 Cheongam-ro Pohang 37673 Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6678-3165","authenticated-orcid":false,"given":"J\u00f6rg","family":"Rademann","sequence":"additional","affiliation":[{"name":"Freie Universit\u00e4t Berlin Department of Biology, Chemistry and Pharmacy  Takustrasse 3\/K\u00f6nigin-Luise-Strasse 2+4 14195 Berlin Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9669-8340","authenticated-orcid":false,"given":"Gerard","family":"Meijer","sequence":"additional","affiliation":[{"name":"Fritz-Haber-Institut der Max-Planck-Gesellschaft Department of Molecular Physics  Faradayweg 4\u20136 14195 Berlin Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9747-0740","authenticated-orcid":false,"given":"Beate","family":"Koksch","sequence":"additional","affiliation":[{"name":"Freie Universit\u00e4t Berlin Department of Biology, Chemistry and Pharmacy  Takustrasse 3\/K\u00f6nigin-Luise-Strasse 2+4 14195 Berlin Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Michael T.","family":"Bowers","sequence":"additional","affiliation":[{"name":"University of California Santa Barbara Department of Chemistry &amp; 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