Путресцин — органічна сполука з формулою (CH2) 4 (NH2)2. Це безбарвна тверда речовина, яка плавиться при кімнатній температурі. Його класифікують як діамін. Разом з кадаверином значною мірою має неприємний запах гниючої плоті, але також сприяє появі інших неприємних запахів.
Путресцин | |
Маса | 1,5E−25 кг[1] |
---|---|
Є мономером | d |
Хімічна формула | C₄H₁₂N₂[1] |
Канонічна формула SMILES | C(CCN)CN[1] |
Температура плавлення | 27 °C |
Наявний у таксона | d, Coryphaena hippurus, E. crassipes, d, M. domestica, d, d, N. tabacum, d, d, A. sativa, B. mori, d, d, C. roseus, C. arietinum, C. intybus, E. cannabinum, d, G. max, d, d, d, d, H. pomatia, H. vulgare, H. verticillata, H. morsus-ranae, L. sativus, N. alata, d, O. sativa, P. palustre, P. glauca, P. sativum, d, P. tetragonolobus, d, J. carniolica, d, d, S. sylvaticus, S. vernalis, S. vulgaris, d, T. thermophilus, T. natans, T. aestivum, U. intermedia, Z. mays, d, A. belladonna, d, C. maxima, d, D. stramonium, H. communis, H. fasciculare, H. sapiens, d, C. elegans, J. vulgaris, D. caryophyllus, S. oleracea, L. albus, P. vulgaris, V. faba, S. tuberosum, E. coli, Chlamydomonas reinhardtii і V. vinifera |
Фізично взаємодіє з | d[57] і d[57] |
Путресцин у Вікісховищі |
Виробництво
Путресцин отримують у промислових масштабах гідруванням сукцинонітрилу.
Досліджено біотехнологічне виробництво путресцину з відновлюваної сировини. Описано метаболічно сконструйований штам Escherichia coli, який продукує путресцин у високих концентраціях у середовищі мінеральних солей глюкози.
Біохімія
Спермідинсинтаза використовує путресцин і S-аденозилметіонінамін (декарбоксильований S-аденозилметіонін) для виробництва спермідину. Спермідин, своєю чергою, поєднується з іншим S -аденозилметіонінаміном і перетворюється на .
Путресцин у невеликих кількостях синтезується здоровими живими клітинами під дією орнітиндекарбоксилази.
Путресцин синтезується біологічно двома різними шляхами, обидва починаються з аргініну.
- В одному шляху аргінін перетворюється на агматин. Перетворення каталізується ферментом аргініндекарбоксилазою (ADC). Агматин перетворюється на N-карбамоїлпутресцин за допомогою агматин іміно гідроксилази (АІГ). Нарешті, N-карбамоїлпутресцин гідролізується з утворенням путресцину.
- У другому шляху аргінін перетворюється на орнітин, а потім орнітин перетворюється на путресцин за допомогою орнітиндекарбоксилази (ODC).
Виникнення
Путресцин міститься в усіх організмах. Путресцин широко зустрічається в рослинних тканинах, часто є найпоширенішим поліаміном, присутнім в організмі. Роль путресцину в розвитку добре задокументована, але останні дослідження показали, що путресцин також відіграє певну роль у реакціях рослин на стрес як на біотичні, так і на абіотичні стресори. Відсутність путресцину в рослинах пов'язана зі збільшенням популяції як паразитів, так і грибів у рослинах.
Використання
Путресцин реагує з адипіновою кислотою, утворюючи поліамідний нейлон 46, який DSM продає під торговою назвою Станил.
Застосування путресцину, поряд з іншими поліамінами, може бути використано для продовження терміну зберігання плодів шляхом затримки процесу дозрівання. Доведено, що передзбиральне внесення путресцину підвищує стійкість рослин до високих температур і посухи. Обидва ці ефекти, здається, є результатом зниження виробництва етилену після екзогенного впливу путресцину.
Історія
Путресцин і кадаверин вперше описані в 1885 році берлінським лікарем Людвігом Брігером (1849–1919).
Токсичність
У щурів путресцин має низьку гостру пероральну токсичність 2000 мг/кг маси тіла, з рівнем неспостережуваних побічних ефектів 2000 ppm (180 мг/кг маси тіла/добу).
Подальше читання
- Haglund, William (1996). Forensic taphonomy: The Postmortem Fate of Human Remains. CRC Press. с. 100. ISBN .
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- Khan, A.S.; Z. Singh (May 2008). . Acta Horticulturae (768): 125—133. doi:10.17660/ActaHortic.2008.768.14. ISSN 0567-7572. Архів оригіналу за 2 червня 2018. Процитовано 4 червня 2023.
- Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" [Further investigations into ptomaines] (Berlin, Germany: August Hirschwald, 1885), page 43. From page 43: Ich nenne dasselbe Putrescin, von putresco, faul werden, vermodern, verwesen. (I call this [compound] "putrescine", from [the Latin word] putresco, to become rotten, decay, rot.)
- Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" [Further investigations into ptomaines] (Berlin, Germany: August Hirschwald, 1885), page 39.
- Til, H.P.; Falke, H.E.; Prinsen, M.K.; Willems, M.I. (1997). Acute and subacute toxicity of tyramine, spermidine, spermine, putrescine and cadaverine in rats. Food and Chemical Toxicology. 35 (3–4): 337—348. doi:10.1016/S0278-6915(97)00121-X. ISSN 0278-6915. PMID 9207896.
Посилання
- Путресцин MS Spectrum
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Putrescin organichna spoluka z formuloyu CH2 4 NH2 2 Ce bezbarvna tverda rechovina yaka plavitsya pri kimnatnij temperaturi Jogo klasifikuyut yak diamin Razom z kadaverinom znachnoyu miroyu maye nepriyemnij zapah gniyuchoyi ploti ale takozh spriyaye poyavi inshih nepriyemnih zapahiv PutrescinMasa1 5E 25 kg 1 Ye monomeromdHimichna formulaC H N 1 Kanonichna formula SMILESC CCN CN 1 Temperatura plavlennya27 CNayavnij u taksonad Coryphaena hippurus E crassipes d M domestica d d N tabacum d d A sativa B mori d d C roseus C arietinum C intybus E cannabinum d G max d d d d H pomatia H vulgare H verticillata H morsus ranae L sativus N alata d O sativa P palustre P glauca P sativum d P tetragonolobus d J carniolica d d S sylvaticus S vernalis S vulgaris d T thermophilus T natans T aestivum U intermedia Z mays d A belladonna d C maxima d D stramonium H communis H fasciculare H sapiens d C elegans J vulgaris D caryophyllus S oleracea L albus P vulgaris V faba S tuberosum E coli Chlamydomonas reinhardtii i V viniferaFizichno vzayemodiye zd 57 i d 57 Putrescin u VikishovishiVirobnictvoPutrescin otrimuyut u promislovih masshtabah gidruvannyam sukcinonitrilu Doslidzheno biotehnologichne virobnictvo putrescinu z vidnovlyuvanoyi sirovini Opisano metabolichno skonstrujovanij shtam Escherichia coli yakij produkuye putrescin u visokih koncentraciyah u seredovishi mineralnih solej glyukozi BiohimiyaSpermidinsintaza vikoristovuye putrescin i S adenozilmetioninamin dekarboksilovanij S adenozilmetionin dlya virobnictva spermidinu Spermidin svoyeyu chergoyu poyednuyetsya z inshim S adenozilmetioninaminom i peretvoryuyetsya na Putrescin u nevelikih kilkostyah sintezuyetsya zdorovimi zhivimi klitinami pid diyeyu ornitindekarboksilazi Putrescin sintezuyetsya biologichno dvoma riznimi shlyahami obidva pochinayutsya z argininu V odnomu shlyahu arginin peretvoryuyetsya na agmatin Peretvorennya katalizuyetsya fermentom arginindekarboksilazoyu ADC Agmatin peretvoryuyetsya na N karbamoyilputrescin za dopomogoyu agmatin imino gidroksilazi AIG Nareshti N karbamoyilputrescin gidrolizuyetsya z utvorennyam putrescinu U drugomu shlyahu arginin peretvoryuyetsya na ornitin a potim ornitin peretvoryuyetsya na putrescin za dopomogoyu ornitindekarboksilazi ODC ViniknennyaPutrescin mistitsya v usih organizmah Putrescin shiroko zustrichayetsya v roslinnih tkaninah chasto ye najposhirenishim poliaminom prisutnim v organizmi Rol putrescinu v rozvitku dobre zadokumentovana ale ostanni doslidzhennya pokazali sho putrescin takozh vidigraye pevnu rol u reakciyah roslin na stres yak na biotichni tak i na abiotichni stresori Vidsutnist putrescinu v roslinah pov yazana zi zbilshennyam populyaciyi yak parazitiv tak i gribiv u roslinah VikoristannyaPutrescin reaguye z adipinovoyu kislotoyu utvoryuyuchi poliamidnij nejlon 46 yakij DSM prodaye pid torgovoyu nazvoyu Stanil Zastosuvannya putrescinu poryad z inshimi poliaminami mozhe buti vikoristano dlya prodovzhennya terminu zberigannya plodiv shlyahom zatrimki procesu dozrivannya Dovedeno sho peredzbiralne vnesennya putrescinu pidvishuye stijkist roslin do visokih temperatur i posuhi Obidva ci efekti zdayetsya ye rezultatom znizhennya virobnictva etilenu pislya ekzogennogo vplivu putrescinu IstoriyaPutrescin i kadaverin vpershe opisani v 1885 roci berlinskim likarem Lyudvigom Brigerom 1849 1919 ToksichnistU shuriv putrescin maye nizku gostru peroralnu toksichnist 2000 mg kg masi tila z rivnem nesposterezhuvanih pobichnih efektiv 2000 ppm 180 mg kg masi tila dobu Podalshe chitannyaHaglund William 1996 Forensic taphonomy The Postmortem Fate of Human Remains CRC Press s 100 ISBN 0 8493 9434 1 Primitkiputrescine d Track Q278487 Bradley J Williams A J Andrew S I D Lang Jean Claude Bradley Open Melting Point Dataset Figshare 2014 doi 10 6084 M9 FIGSHARE 1031637 V2 d Track Q17021355d Track Q69644056d Track Q17013516d Track Q4777220d Track Q4758469 CN C SI P MJ K et al Occurrence of cadaverine in hairy roots of 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