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For two investigated conjugates that show ultrafast electron transfer, A23C-Ru and K29C-Ru, analysis by circular dichroism spectroscopy, CD, demonstrated site-specific chiral discrimination as a factor emerging from the close association between [Ru(bpy)<jats:sub>3<\/jats:sub>]<jats:sup>2+<\/jats:sup> and heme cofactors. CD analysis showed the A23C-Ru and K29C-Ru conjugates to have distinct, but opposite, stereoselectivity for the <jats:italic>\u039b<\/jats:italic> and <jats:italic>\u0394<\/jats:italic>-Ru(bpy)<jats:sub>2<\/jats:sub>(Br-bpy) enantiomers, with enantiomeric excesses of 33.1% and 65.6%, respectively. In contrast, Ru(bpy)<jats:sub>2<\/jats:sub>(Br-bpy) conjugation to a protein site with high flexibility, represented by the E39C-Ru construct, exhibited a nearly negligible chiral selectivity, measured by an enantiomeric excess of 4.2% for the <jats:italic>\u039b<\/jats:italic> enantiomer. Molecular dynamics simulations showed that site-specific stereoselectivity reflects steric constraints at the conjugating sites and that a high degree of chiral selectivity correlates to reduced structural disorder for [Ru(bpy)<jats:sub>3<\/jats:sub>]<jats:sup>2+<\/jats:sup> in the linked\u00a0assembly. This work identifies chiral discrimination as means to achieve site-specific, precise geometric positioning of introduced photosensitizers relative to the heme cofactors in manner that mimics the tuning of cofactors in photosynthesis.<\/jats:p>","DOI":"10.1007\/s11120-019-00697-8","type":"journal-article","created":{"date-parts":[[2020,1,10]],"date-time":"2020-01-10T13:02:44Z","timestamp":1578661364000},"page":"99-113","update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Examination of abiotic cofactor assembly in photosynthetic biomimetics: site-specific stereoselectivity in the conjugation of a ruthenium(II) tris(bipyridine) photosensitizer to a multi-heme protein"],"prefix":"10.1007","volume":"143","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-7256-3126","authenticated-orcid":false,"given":"Nina S.","family":"Ponomarenko","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9867-8044","authenticated-orcid":false,"given":"Oleksandr","family":"Kokhan","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5301-9483","authenticated-orcid":false,"given":"Phani R.","family":"Pokkuluri","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3132-1179","authenticated-orcid":false,"given":"Karen L.","family":"Mulfort","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2784-4954","authenticated-orcid":false,"given":"David M.","family":"Tiede","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"297","published-online":{"date-parts":[[2020,1,10]]},"reference":[{"key":"697_CR1","doi-asserted-by":"publisher","first-page":"1613","DOI":"10.1002\/jcc.20079","volume":"25","author":"F Autenrieth","year":"2004","unstructured":"Autenrieth F, Tajkhorshid E, Baudry J, Luthey-Schulten Z (2004) Classical force field parameters for the heme prosthetic group of cytochrome c. 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