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Unlike linear fatty acyl groups, the branched and unsaturated structure of isoprenoids introduces complex sterics and restricted conformational degrees of freedom. These unique features enable the fine\u2010tuning of membrane behaviors, including lateral partitioning, packing defects, and hydrophobic mismatches, which can dictate biological outcomes. Focusing on biocatalytic prenylation, this review summarizes eukaryotic, cyanobactin, and\n                    <jats:italic>trans<\/jats:italic>\n                    \u2010isoprenyl diphosphate synthase (\n                    <jats:italic>trans<\/jats:italic>\n                    \u2010IDS)\u2010like prenyltransferases. We examine how active\u2010site motifs govern specificity for both the amino acid acceptor and the donor isoprenoid, thereby enabling the use of longer\u2010chain variants and geometric isomers, as well as regioselective modification of tryptophan. Furthermore, we compare the biophysical properties of emerging tryptophan\n                    <jats:italic>C<\/jats:italic>\n                    \u2010prenylation with those of conventional cysteine\n                    <jats:italic>S<\/jats:italic>\n                    \u2010prenylation and linear fatty acylation, highlighting their distinct roles in modulating polypeptide function and behavior. Finally, we focus on applications of enzymatic prenylation in antimicrobial development and protein engineering, outlining future opportunities for AI\u2010guided design of prenylated peptides and proteins.\n                  <\/jats:p>","DOI":"10.1002\/chem.70995","type":"journal-article","created":{"date-parts":[[2026,4,10]],"date-time":"2026-04-10T07:07:19Z","timestamp":1775804839000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Enzymatic Prenylation of Proteins and Peptides: From Cysteine\n                    <i>S<\/i>\n                    \u2010Prenylation to Tryptophan\u2010Selective Biocatalysis"],"prefix":"10.1002","volume":"32","author":[{"given":"Daisuke","family":"Fujinami","sequence":"first","affiliation":[{"name":"Graduate School of Integrated Pharmaceutical and Nutritional Sciences University of Shizuoka  Shizuoka Shizuoka 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