{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2023,3,6]],"date-time":"2023-03-06T16:52:43Z","timestamp":1678121563933},"reference-count":19,"publisher":"Institute of Biochemistry","issue":"4","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["BIOMED KHIM"],"published-print":{"date-parts":[[2014,7]]},"abstract":"<jats:p>The preparative microbial synthesis of amino acids labelled with stable isotopes, including deuterium ( 2 H), suitable for biomedical applications by methylotrophic bacteria was studied using L-phenylalanine as example. This amino acid is secreted by Gram-negative aerobic facultative methylotrophic bacteria Brevibacterium methylicum, assimilating methanol via ribulose-5-monophosphate (RMP) cycle of assimilation of carbon, The data on adaptation of L-phenylalanine secreted by methylotrophic bacterium \u0412. methylicum to the maximal concentration of deuterium in the growth medium with 98% 2 \u041d 2 O and 2% [ 2 \u041d]methanol, and biosynthesis of deuterium labelled L-phenylalanine With different levels of enrichment are presented. The strain was adapted by means of plating initial cells on firm (2% agarose) minimal growth media with an increasing gradient of 2 \u041d 2 O concentration from 0; 24.5; 49.0; 73.5 up to 98% 2 \u041d 2 O followed by subsequent selection of separate colonies stable to the action of 2 \u041d 2 O. These colonies were capable to produce L-phenylalanine. L-phenylalanine was extracted from growth medium by extraction with isopropanol with the subsequent cristallization in ethanol (output 0.65 g\/l). The developed method of microbial synthesis allows to obtain deuterium labelled L-phenylalanine with different levels of isotopic enrichment, depending on concentration of 2 \u041d 2 O in growth media, from 17% (on growth medium with 24,5% 2 \u041d 2 O) up to 75% (on growth medium with 98% 2 \u041d 2 O) of deuterium in the molecule that is confirmed with the data of the electron impact (EI) mass- spectrometry analysis of methyl ethers of N-dimethylamino(naphthalene)-5-sulfochloride (dansyl) phenylalanine in these experimental conditions.<\/jats:p>","DOI":"10.18097\/pbmc20146004448","type":"journal-article","created":{"date-parts":[[2015,4,24]],"date-time":"2015-04-24T12:35:43Z","timestamp":1429878943000},"page":"448-461","source":"Crossref","is-referenced-by-count":2,"title":["Microbic synthesis of deuterium labelled L-phenylalanine with different levels of isotopic enrichment by facultative methylotrophic bacterium brevibacterium methylicum with RMP assimilation of carbon"],"prefix":"10.18097","volume":"60","author":[{"given":"O.V.","family":"Mosin","sequence":"first","affiliation":[{"name":"Lomonosov Moscow University of Fine Chemical Technology, Federation"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"V.I.","family":"Shvets","sequence":"additional","affiliation":[{"name":"Lomonosov Moscow University of Fine Chemical Technology, Federation"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"D.A.","family":"Skladnev","sequence":"additional","affiliation":[{"name":"Research Institute for Genetics and Selection of Industrial Microorganisms"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"I.","family":"Ignatov","sequence":"additional","affiliation":[{"name":"Scientific Research Center of Medical Biophysics"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"7443","published-online":{"date-parts":[[2014]]},"reference":[{"key":"ref1","unstructured":"LeMaster D.M. (1990)Annu. Rev. Biophys. Chem., 19, 243-266."},{"key":"ref2","unstructured":"Vertes A. (2003) in: Elements and isotopes: formation, transformation, distribution (Vertes A. (ed.)) Kluwer Acad. Publ, Dordrecht, pp. 111\u2013112."},{"key":"ref3","unstructured":"Crespi H.L. (1986) Biosynthesis and uses of per-deuterated proteins. in: Proceedings of the Second Inter. Symp. On Synthesis and Applications of Isotopically labeled Compounds (Muccino R.R. (ed.)) Elsevier., NY, pp. 111-112."},{"key":"ref4","unstructured":"MacCarthy P. (1985) J. Chem. Educ., 62, 633-638."},{"key":"ref5","unstructured":"Mosin O.V., Skladnev D.A., Egorova T.A., Shvets V.I. (1996) Bioorgan. khim., 22, 856-869."},{"key":"ref6","unstructured":"Kushner D.J., Baker A., Dunstall T.G. (1999) Can. J. Physiol. Pharmacol., 77, 79\u201388."},{"key":"ref7","unstructured":"Skladnev D.A., Mosin O.V., Egorova T.A., Eremin S.V., Shvets V.I. (1996) Biotekhnologiya, \u21165, 25-34."},{"key":"ref8","unstructured":"Mosin O.V. (1996) Issledovanie metodov biotekhnologicheskogo polucheniya aminokislot, belkov i nukleozidov, mechennykh stabilnymi izotopami 2 N i 13 S s vysokimi urovnyami izotopnogo obogashcheniya. Avtoref. diss. kand. khim. nauk. MITKhT im. M.V. Lomonosova, Moskva, s. 1-26."},{"key":"ref9","unstructured":"Dewick P.M. (2009) in: Medicinal Natural Products: A Biosynthetic Approach (Derwik P.M. (ed.)) 3-rd Edition, John Wiley & Sons Ltd, Chichester, UK, pp. 137\u2013186."},{"key":"ref10","unstructured":"Karnaukhova E.N., Mosin O.V., Reshetova O.S. (1993) Amino Acids, 5, 125."},{"key":"ref11","unstructured":"Mosin O.V., Skladnev D.A., Egorova T.A., Yurkevich A.M., Shvets V.I. (1996) Biotekhnologiya, \u21163, 3-12."},{"key":"ref12","unstructured":"Mosin O.V., Karnaukhova E.N., Pshenichnikova A.B., Skladnev D.A., Akimova O.L. (1993) Biotekhnologiya, \u21169, 16-20."},{"key":"ref13","doi-asserted-by":"publisher","unstructured":"de Boer L., Harder W., Dijkhuizen L. (1988) Arch. Microbiol., 149, 459-465.","DOI":"10.1007\/BF00425588"},{"key":"ref14","unstructured":"Bokhinski R. (1987) Sovremennye vozzreniya v biokhimii (per. s angl.), Mir, Moskva, s. 443-444."},{"key":"ref15","doi-asserted-by":"publisher","unstructured":"Herrmann K.M., Weawer L.M. (1999) The Shikimate Pathway. Annual Rewiew of Plant Physiology and Plant Molecular Biology, 50, 473-503.","DOI":"10.1146\/annurev.arplant.50.1.473"},{"key":"ref16","unstructured":"Rouse B., Azen B., Koch R., Matalon R., Hanley W., de la Cruz F., Trefz F., Friedman E., Shifrin H. (1997) Am. J. Med. Gen., 69, 89\u201395."},{"key":"ref17","doi-asserted-by":"publisher","unstructured":"Mosin O.V., Skladnev D.A., Shvets V.I. (1998) Bioscience, Biotechnology and Biochemistry, 62, 225-229.","DOI":"10.1271\/bbb.62.225"},{"key":"ref18","unstructured":"Mosin O.V., Skladnev D.A., Shvets V.I. (2000) Biotekhnologiya, \u211610, 16-23."},{"key":"ref19","unstructured":"Trotsenko Yu.A. (1987) Biokhimiya i fiziologiya metilotrofnykh mikroorganizmov. Sb. nauchn. stat. AN SSSR, Institut biokhimii i fiziologii mikroorganizmov, Pushchino, s. 15."}],"container-title":["Biomeditsinskaya Khimiya"],"original-title":[],"language":"ru","deposited":{"date-parts":[[2019,9,16]],"date-time":"2019-09-16T15:50:48Z","timestamp":1568649048000},"score":1,"resource":{"primary":{"URL":"http:\/\/pbmc.ibmc.msk.ru\/en\/article-en\/PBMC-2014-60-4-448"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2014]]},"references-count":19,"journal-issue":{"issue":"4","published-online":{"date-parts":[[2014]]},"published-print":{"date-parts":[[2014]]}},"URL":"https:\/\/doi.org\/10.18097\/pbmc20146004448","relation":{},"ISSN":["2310-6905","2310-6972"],"issn-type":[{"value":"2310-6905","type":"electronic"},{"value":"2310-6972","type":"print"}],"subject":[],"published":{"date-parts":[[2014]]}}}