{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,26]],"date-time":"2026-05-26T05:07:07Z","timestamp":1779772027774,"version":"3.53.1"},"reference-count":33,"publisher":"Wiley","issue":"9","license":[{"start":{"date-parts":[[2026,5,15]],"date-time":"2026-05-15T00:00:00Z","timestamp":1778803200000},"content-version":"vor","delay-in-days":1,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2026,5,14]],"date-time":"2026-05-14T00:00:00Z","timestamp":1778716800000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/100010269","name":"WT","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100010269","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100010661","name":"Horizon 2020 Framework Programme","doi-asserted-by":"publisher","award":["Lysomod MS\u2010C RISE 734825"],"award-info":[{"award-number":["Lysomod MS\u2010C RISE 734825"]}],"id":[{"id":"10.13039\/100010661","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100011710","name":"NPRF","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100011710","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemMedChem"],"published-print":{"date-parts":[[2026,5,14]]},"abstract":"<jats:p>\n                    N\u2010acetyl\u2010L\u2010leucine (levacetylleucine, ALL) is the neuroprotective enantiomer of the racemic antivertigo drug, Tanganil (acetyl\u2010DL\u2010leucine, ADLL). ALL has recently been clinically repurposed for the treatment of Niemann Pick disease type C1, a disorder characterised by lysosomal accumulation of glycolipids and cholesterol. Isotopically labelled ALL was required, as well as its negative control, D\u2010enantiomer (ADL), to monitor the in vivo metabolic fate of the drug and to distinguish it from endogenous leucine and associated metabolites. Here, we describe the synthesis of N\u2010acetyl\u2010D\u2010 and \u2010L\u2010leucine\u2010\n                    <jats:sup>13<\/jats:sup>\n                    C\n                    <jats:sub>6<\/jats:sub>\n                    , as well as N\u2010acetyl\u2010L\u2010leucine\u2010\n                    <jats:sup>13<\/jats:sup>\n                    C\n                    <jats:sub>1<\/jats:sub>\n                    , by N\u2010acetylation of their amino acid precursors, their spectroscopic characterisation and stereochemical and stability studies. These investigations found that formation of the products, as well as their water\u2010soluble sodium salt formulation, occurs without compromising stereochemical integrity.\n                  <\/jats:p>","DOI":"10.1002\/cmdc.70295","type":"journal-article","created":{"date-parts":[[2026,5,16]],"date-time":"2026-05-16T01:50:39Z","timestamp":1778896239000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Synthesis of N\u2010Acetyl\u2010D\u2010 and \u2010L\u2010Leucine\u2010\n                    <sup>13<\/sup>\n                    C\n                    <sub>6<\/sub>\n                    Tool Compounds in Neurodegenerative Disease"],"prefix":"10.1002","volume":"21","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-6601-5975","authenticated-orcid":false,"given":"Damien","family":"Crepin","sequence":"first","affiliation":[{"name":"Sussex Drug Discovery Centre School of Life Sciences University of Sussex  Falmer UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2187-3850","authenticated-orcid":false,"given":"Andrew","family":"McGown","sequence":"additional","affiliation":[{"name":"Sussex Drug Discovery Centre School of Life Sciences University of Sussex  Falmer UK"},{"name":"Department of Chemistry School of Life Sciences University of Sussex  Falmer UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1304-6051","authenticated-orcid":false,"given":"Dawn","family":"Shepherd","sequence":"additional","affiliation":[{"name":"Department of Pharmacology University of Oxford  Oxford UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0009-8818-2518","authenticated-orcid":false,"given":"Rebecca","family":"Braine","sequence":"additional","affiliation":[{"name":"Department of Pharmacology University of Oxford  Oxford UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4606-3640","authenticated-orcid":false,"given":"Manvendra","family":"Sharma","sequence":"additional","affiliation":[{"name":"Department of Chemistry School of Life Sciences University of Sussex  Falmer UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1986-0302","authenticated-orcid":false,"given":"Jordan","family":"Nafie","sequence":"additional","affiliation":[{"name":"BioTools Inc.  West Palm Beach FL USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jo\u00e3o Gabriel","family":"Ribeiro","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Bath  Bath UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2200-550X","authenticated-orcid":false,"given":"G. Dan","family":"Panto\u015f","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Bath  Bath UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9591-9391","authenticated-orcid":false,"given":"Grant","family":"Churchill","sequence":"additional","affiliation":[{"name":"Department of Pharmacology University of Oxford  Oxford UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7614-0403","authenticated-orcid":false,"given":"Frances M.","family":"Platt","sequence":"additional","affiliation":[{"name":"Department of Pharmacology University of Oxford  Oxford UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5231-8836","authenticated-orcid":false,"given":"John","family":"Spencer","sequence":"additional","affiliation":[{"name":"Sussex Drug Discovery Centre School of Life Sciences University of Sussex  Falmer UK"},{"name":"Department of Chemistry School of Life Sciences University of Sussex  Falmer UK"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,5,15]]},"reference":[{"key":"e_1_2_10_2_1","doi-asserted-by":"publisher","DOI":"10.1046\/j.0953-816x.2000.01447.x"},{"key":"e_1_2_10_3_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00415-013-7016-x"},{"key":"e_1_2_10_4_1","doi-asserted-by":"publisher","DOI":"10.1186\/s40673-016-0046-2"},{"key":"e_1_2_10_5_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-024-51502-7"},{"key":"e_1_2_10_6_1","doi-asserted-by":"publisher","DOI":"10.1186\/s12883-025-04451-7"},{"key":"e_1_2_10_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejphar.2015.11.041"},{"key":"e_1_2_10_8_1","doi-asserted-by":"publisher","DOI":"10.1093\/braincomms\/fcaa148"},{"key":"e_1_2_10_9_1","doi-asserted-by":"publisher","DOI":"10.1002\/trc2.70029"},{"key":"e_1_2_10_10_1","doi-asserted-by":"publisher","DOI":"10.1007\/s44162-025-00076-z"},{"key":"e_1_2_10_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tips.2025.02.003"},{"key":"e_1_2_10_12_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41598-021-95255-5"},{"key":"e_1_2_10_13_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11064-007-9444-4"},{"key":"e_1_2_10_14_1","doi-asserted-by":"publisher","DOI":"10.1152\/ajpendo.1980.238.5.E473"},{"key":"e_1_2_10_15_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.7302583"},{"key":"e_1_2_10_16_1","doi-asserted-by":"publisher","DOI":"10.1016\/0003-2697(88)90036-X"},{"key":"e_1_2_10_17_1","doi-asserted-by":"publisher","DOI":"10.2174\/1874471009666161230114954"},{"key":"e_1_2_10_18_1","doi-asserted-by":"publisher","DOI":"10.1039\/a907598d"},{"key":"e_1_2_10_19_1","doi-asserted-by":"publisher","DOI":"10.1006\/abio.1996.0293"},{"key":"e_1_2_10_20_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chembiol.2018.09.004"},{"key":"e_1_2_10_21_1","doi-asserted-by":"publisher","DOI":"10.1042\/BJ20082198"},{"key":"e_1_2_10_22_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00726-015-1920-6"},{"key":"e_1_2_10_23_1","doi-asserted-by":"publisher","DOI":"10.14814\/phy2.12479"},{"key":"e_1_2_10_24_1","doi-asserted-by":"publisher","DOI":"10.1371\/journal.pone.0229585"},{"key":"e_1_2_10_25_1","doi-asserted-by":"publisher","DOI":"10.5194\/mr-1-237-2020"},{"key":"e_1_2_10_26_1","doi-asserted-by":"publisher","DOI":"10.1002\/chir.10287"},{"key":"e_1_2_10_27_1","doi-asserted-by":"publisher","DOI":"10.1366\/11-06321"},{"key":"e_1_2_10_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacsau.4c00962"},{"key":"e_1_2_10_29_1","doi-asserted-by":"publisher","DOI":"10.1039\/c2ob25109d"},{"key":"e_1_2_10_30_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-025-57145-6"},{"key":"e_1_2_10_31_1","first-page":"731","volume-title":"Handbook of Vibrational Spectroscopy","author":"Nafie L. 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