Share to: share facebook share twitter share wa share telegram print page

硫辛酸

硫辛酸
IUPAC名
(R)-5-(1,2-dithiolan-3-yl)pentanoic acid
识别
CAS号 1200-22-2 ?
PubChem 6112
SMILES
 
  • OC(=O)CCCC[C@@H]1CCSS1
MeSH Lipoic+acid
性质
化学式 C8H14O2S2
摩尔质量 206.33 g·mol⁻¹
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

6,8-二硫辛酸,簡稱硫辛酸(lipoic acid),为含八碳脂酸,在6、8位上有二硫键相连(C6和C8上的原子被二硫键取代),有氧化、还原二型。6、8位上巯基脱氢为氧化型硫辛酸(两个硫原子通过二硫键相连),加氢变成还原型称为二氢硫辛酸(二硫键还原为巯基)。硫辛酸虽然不属于维生素,但其可作为辅酶参与机体内物质代谢过程中酰基转移,起到递氢和转移酰基的作用(即作为氢载体和酰基载体),具有与维生素相似的功能(类维生素),因此也被生物化学教材列入维生素中讲述。

化学结构与性质

硫辛酸以闭环二硫化物形式和开链还原形式两种结构混合物存在,这两种形式通过氧化-还原循环相互转换,像生物素一样,硫辛酸事实上常常不游离存在,而是以其羧基同酶分子(如二氢硫辛酸乙酰转移酶)中赖氨酸残基的ε-NH2基以酰胺键共价结合(结构上与生物胞素十分相似)。催化形成硫辛酰胺键的酶需要ATP,并且作为反应产物产生硫辛酰胺-酶偶联物、AMP焦磷酸。硫辛酸1951年被L. J. Reed等分离成晶体。因是一种含硫的脂肪酸,故有人将其归属于脂溶性维生素。但由于在体内代谢中与TPP、NAD+等辅酶一起参加生化反应,因此,根据结构与功能的统一性,也有人将其归入B族维生素。硫辛酸是既具水溶性(微溶)又具脂溶性的淡黄色晶体,外消旋硫辛酸熔点在60~61℃,沸点为160~165℃。

功能

硫辛酸作为辅酶,在两个关键性的氧化脱羧反应中起作用,即在丙酮酸脱氢酶复合体α-酮戊二酸脱氢酶复合体中,催化酰基的产生和转移。硫辛酸可以接受酰基与丙酮酸的乙酰基,形成一个硫酯键,然后将乙酰基转移到辅酶A分子的硫原子上。形成辅基的二氢硫辛酰胺可再经二氢硫辛酰胺脱氢酶(需要NAD+)氧化,重新生成氧化型硫辛酰胺。α-硫辛酸含有双硫五元环结构,电子密度很高,具有显著的亲电子性和与自由基反应的能力,因此它具有抗氧化性,具有极高的保健功能和医用价值(如抗脂肪肝和降低血浆胆固醇的作用)。此外,硫辛酸的巯基很容易进行氧化还原反应,故可保护巯基酶免受重金属离子的毒害。硫辛酸在自然界广泛分布,酵母细胞中含量尤为丰富。在食物中硫辛酸常和维生素B1同时存在。人体可以合成。目前,尚未发现人类有硫辛酸的缺乏症。

疾病

结合性丙二酸及甲基丙二酸血症 (CMAMMA)

在因 ACSF3 缺乏症而结合性丙二酸及甲基丙二酸血症(CMAMMA)中,线粒体脂肪酸合成(mtFASII)(脂酸生物合成的前体反应)受到损害[1][2]。结果导致丙酮酸脱氢酶复合物(PDC)和α-酮戊二酸脱氢酶复合物(α-KGDHC)等重要线粒体酶的脂酰化程度降低[2]。补充硫辛酸并不能恢复线粒体的功能[3][2]

参考文献

  1. ^ Levtova, Alina; Waters, Paula J.; Buhas, Daniela; Lévesque, Sébastien; Auray‐Blais, Christiane; Clarke, Joe T.R.; Laframboise, Rachel; Maranda, Bruno; Mitchell, Grant A.; Brunel‐Guitton, Catherine; Braverman, Nancy E. Combined malonic and methylmalonic aciduria due to ACSF3 mutations: Benign clinical course in an unselected cohort. Journal of Inherited Metabolic Disease. 2019-01, 42 (1). ISSN 0141-8955. doi:10.1002/jimd.12032 (英语). 
  2. ^ 2.0 2.1 2.2 Wehbe, Zeinab; Behringer, Sidney; Alatibi, Khaled; Watkins, David; Rosenblatt, David; Spiekerkoetter, Ute; Tucci, Sara. The emerging role of the mitochondrial fatty-acid synthase (mtFASII) in the regulation of energy metabolism. Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids. 2019-11, 1864 (11) [2023-12-09]. doi:10.1016/j.bbalip.2019.07.012. (原始内容存档于2022-06-19) (英语). 
  3. ^ Hiltunen, J. Kalervo; Autio, Kaija J.; Schonauer, Melissa S.; Kursu, V.A. Samuli; Dieckmann, Carol L.; Kastaniotis, Alexander J. Mitochondrial fatty acid synthesis and respiration. Biochimica et Biophysica Acta (BBA) - Bioenergetics. 2010-06, 1797 (6-7) [2023-12-09]. doi:10.1016/j.bbabio.2010.03.006. (原始内容存档于2022-10-06) (英语). 
Read more information:

2005 single by Echo & the BunnymenStormy WeatherSingle by Echo & the Bunnymenfrom the album Siberia Released5 September 2005RecordedElevator Studios, LiverpoolGenreAlternative rockLength3:07LabelCooking VinylSongwriter(s)Will Sergeant, Ian McCullochProducer(s)Hugh JonesEcho & the Bunnymen singles chronology Make Me Shine (2001) Stormy Weather (2005) In the Margins (2005) Stormy Weather is a single by Echo & the Bunnymen which was released on 5 September 2005 on the Cooking Vinyl …

Комплекс споруд Поштової станції (Житомир) 50°16′09″ пн. ш. 28°38′56″ сх. д. / 50.269166666694772516° пн. ш. 28.64888888891677965° сх. д. / 50.269166666694772516; 28.64888888891677965Координати: 50°16′09″ пн. ш. 28°38′56″ сх. д. / 50.269166666694772516° пн. ш. 28.64888888891677965° сх. …

هذه المقالة يتيمة إذ تصل إليها مقالات أخرى قليلة جدًا. فضلًا، ساعد بإضافة وصلة إليها في مقالات متعلقة بها. (نوفمبر 2023) وادي الذئاب المنسيةمعلومات عامةالمؤلف عمرو عبد الحميداللغة العربيةالبلد  مصرالموضوع لعنة — سفر عبر الزمن — البعث بعد الموت — ذئب رهيب النوع الأدبي رواي

ПейзакPayzac Країна  Франція Регіон Овернь-Рона-Альпи  Департамент Ардеш  Округ Ларжантьєр Кантон Жуаєз Код INSEE 07171 Поштові індекси 07230 Координати 44°27′16″ пн. ш. 4°09′14″ сх. д.H G O Висота 188 - 619 м.н.р.м. Площа 13,7 км² Населення 538 (01-2020[1]) Густота 39,71 ос./км² Розміщ…

Artikel ini membutuhkan rujukan tambahan agar kualitasnya dapat dipastikan. Mohon bantu kami mengembangkan artikel ini dengan cara menambahkan rujukan ke sumber tepercaya. Pernyataan tak bersumber bisa saja dipertentangkan dan dihapus.Cari sumber: Ikonografi manga – berita · surat kabar · buku · cendekiawan · JSTOR Sebuah halaman dari manga Marmalade Boy volume 1 (versi bahasa Jepang) Bagian dari seri tentangAnime dan manga Anime Sejarah Industri Animasi …

Opening in the tip of the root of a tooth Apical foramenApical foramina on a wisdom toothDetailsIdentifiersLatinforamen apicis dentisTA98A05.1.03.050TA2933FMA57159Anatomical terminology[edit on Wikidata] 1. Tooth 2. Enamel 3. Dentin 4. Dental pulp ::5. cameral pulp ::6. root pulp :7. Cementum :8. Crown ::9. Cusp ::10. Sulcus :11. Neck :12. Root ::13. Furcation ::14. Root apex :::15. Apical foramen 16. Gingival sulcus 17. Periodontium :18. Gingiva: ::19…

  هذه المقالة عن مسبار الفضاء ماسنجر. لصفحة توضيح، طالع ماسنجر (توضيح).   ماسنجر ماسنجر (مسبار فضائي)Artist's rendering of MESSENGER orbiting Mercury. ماسنجر (مسبار فضائي)شعار طبيعة المهمة عطارد probe المشغل ناسا رمز التعريف الفلكي 2004-030A رقم دليل القمر الصناعي 28391 الموقع الإلكتروني messenger.jhuapl.edu …

2004 superhero film by Guillermo del Toro HellboyTheatrical release posterDirected byGuillermo del ToroScreenplay byGuillermo del ToroStory by Guillermo del Toro Peter Briggs Based onHellboyby Mike MignolaProduced by Lawrence Gordon Mike Richardson Lloyd Levin Starring Ron Perlman Selma Blair Jeffrey Tambor Karel Roden Rupert Evans John Hurt CinematographyGuillermo NavarroEdited byPeter AmundsonMusic byMarco BeltramiProductioncompanies Lawrence Gordon/Lloyd Levin Productions[1] Dark Hors…

Chikunguña Erupción en pie izquierdo causada por chikunguñaEspecialidad infectologíaSíntomas Fiebre, dolor en las articulacionesDiagnóstico Análisis de sangre para ARN viral o anticuerposDiagnóstico diferencial Dengue, zika[1]​Prevención Control de mosquitos, prevención de picaduras.Sinónimos Artritis epidémica chikunguña Fiebre de chikunguña CHIK[editar datos en Wikidata] Reconstrucción con criomicroscopía electrónica del virus de chikunguña La chikunguña[2]&#…

Bagian dari seri tentangIslam Sunni Rukun iman Tauhid Malaikat Nabi dan Rasul Kitab Hari Akhir Qada dan Qadar Rukun Islam Syahadat Salat Zakat Puasa Haji Khulafaur Rasyidin Abu Bakar Umar bin Khattab Utsman bin 'Affan Ali bin Abi Thalib Mazhab fikih Hanafiyah Malikiyah Syafi'iyah Hanabilah Lainnya Zhahiri Auza'i Tsauri Laitsi Jariri Mazhab akidah Ahli Hadis Atsariyah Ahlur Ra’yi Asy'ariyah Maturidiyah Dalam konteks Ihsan Wajd dan Kasyf (Sufi) Gerakan Barelwi Deobandi Modernisme Islam Modernism…

Notion in Taiwan-China relationsThe One China policy in practice.   People's Republic of China (PRC).   Republic of China (ROC).   Countries recognizing the PRC only.   Countries recognizing the ROC only.   Countries recognizing the PRC, but have semi-formal relations with the ROC.   Countries without reported relations with either the PRC or the ROC. One Country on Each SideTraditional Chinese一邊一國Simplified Chinese一边…

Ini adalah sebuah nama Indonesia yang tidak menggunakan nama keluarga. Nama Soekarnoputri adalah sebuah patronimik. Rachmawati SoekarnoputriRachmawati, 2020Anggota Dewan Pertimbangan Presiden Bidang PolitikMasa jabatan10 April 2007 (2007-04-10) – 20 Oktober 2009 (2009-10-20)PresidenSusilo Bambang YudhoyonoKetuaAli AlatasTiopan Bernhard SilalahiPendahuluTidak ada, jabatan baruPenggantiRyaas RasyidKetua Umum Partai Pelopor ke-1Masa jabatan29 Agustus 2002 (2002-08-29)&…

Pour un article plus général, voir Barrage de Sivens. La chronologie du projet de barrage de Sivens relate chronologiquement les différents événements associés au projet de barrage de Sivens : des premières études à l'enquête publique, puis la contestation avec divers recours en justice, l'occupation du site et la manifestation du 25 octobre 2014 qui donne lieu à de violents affrontements entre certains activistes et les forces de l'ordre, et aboutit à la mort du manifestant Ré…

Hospital in London, England Hospital in London , EnglandCentral Middlesex HospitalLondon North West University Healthcare NHS TrustMain entranceLocation within BrentGeographyLocationActon Lane, Park Royal, London NW10 7NS, EnglandOrganisationCare systemNational Health ServiceTypeDistrict generalAffiliated universityImperial College LondonServicesEmergency departmentNoBeds214LinksWebsitewww.lnwh.nhs.uk/central-middlesex-hospital ListsHospitals in England Central Middlesex Hospital is in the centr…

Point-and-click adventure game This article is about the video game. For the Samaritan Gnostic sometimes known as Simon the Sorcerer, see Simon Magus. For the series of the same name, see Simon the Sorcerer (series). 1993 video gameSimon the SorcererThe box art for the Amiga 1200 release.Developer(s)Adventure SoftPublisher(s)Adventure SoftDirector(s)Mike WoodroffeProducer(s)Mike Woodroffe, Alan BridgmanDesigner(s)Simon WoodroffeProgrammer(s)Alan BridgmanArtist(s)Paul DrummondWriter(s)Simon Woodr…

Small toy gun used to fire a fragment of potato For the larger gun which fires whole potatoes, see Potato cannon. A typical factory-made toy die-cast spud gun. The cap attached to the muzzle converts it into a water pistol. A spud gun is a small toy gun used to fire a fragment of potato. To operate, one punctures the surface of a potato with the gun's hollow tip and pries out a small pellet which fits in the muzzle. Squeezing the grip causes a small build-up of air pressure inside the toy which …

Bandeira das Nações Unidas Proporção 2:3 ou 3:5[nota 1] Adoção 7 de Dezembro de 1946 Criador Donal McLaughlin (somente emblema) Descrição Um emblema em branco da ONU (mapa-múndi rodeado por dois ramos de oliva) sobre um fundo em azul claro. Tipo Internacional A bandeira das Nações Unidas consiste no emblema que representa a projeção equidistante azimutal branca do mapa-múndi, centrada no Polo Norte, com dois ramos de oliveira brancos colocados à sua direita e à esquerda, localiza…

This article is about the 1991 Hindi film. For the 1957 Hindi film, see Bhabhi (1957 film). 1991 Indian filmBhabhi भाभीTheatrical release posterDirected byKishore VyasWritten byNawab ArzooProduced byJawaharlal BafnaVasant DoshiStarringGovindaBhanupriyaJuhi ChawlaCinematographyU.S. SrivastavaMusic byAnu MalikRelease date 23 August 1991 (1991-08-23) (India) CountryIndiaLanguageHindi Bhabhi is a 1991 Indian Bollywood film directed by Kishore Vyas and produced by Jawaharla…

Iranian Prime Minister Not to be confused with Hassan Ali Mansur. For the village in Iran, see Ali Mansur, Iran. Ali Mansur25th Prime Minister of IranIn office4 April 1950 – 25 June 1950MonarchMohammad Reza PahlaviPreceded byMohammad Sa'edSucceeded byAli RazmaraIn office26 June 1940 – 27 August 1941MonarchReza ShahPreceded byAhmad Matin-DaftariSucceeded byMohammad-Ali Foroughi Personal detailsBorn1886Tehran, Qajar IranDied8 December 1974(1974-12-08) (aged 87–88)T…

Polyhedral compound Compound of two snub icosidodecadodecahedra Type Uniform compound Index UC75 Polyhedra 2 snub icosidodecadodecahedra Faces 40+120 triangles,24 pentagons,24 pentagrams Edges 360 Vertices 120 Symmetry group icosahedral (Ih) Subgroup restricting to one constituent chiral icosahedral (I) 3D model of the compound of two snub icosidodecahedra The compound of two snub icosidodecadodecahedra is a uniform polyhedron compound. It's composed of the 2 enantiomers of the snub icosidodecad…

Kembali kehalaman sebelumnya

Lokasi Pengunjung: 44.212.93.133