Altroosi

Altroosi
Tunnisteet
CAS-numero 1990-29-0
SMILES C(C(C(C(C(C=O)O)O)O)O)O [1]
Ominaisuudet
Molekyylikaava C6H12O6
Moolimassa 180,156 g/mol
Sulamispiste 103,5 °C[2]
Liukoisuus veteen Liukenee veteen

Altroosi (C6H12O6) on aldoheksooseihin kuuluva monosakkaridi. Luonnossa esiintyvänä se on hyvin harvinainen.

Esiintyminen, ominaisuudet ja synteesi

D-Altroosin pyranoosien ja furanoosien rakenteet

Altroosi esiintyy luonnossa ainoastaan erittäin harvinaisena. D-Altroosia ei ole tavattu vielä mistään eliöstä, mutta L-altroosin on havaittu olevan osa Butyrivibrio fibrisolvens -bakteerin, jota elää märehtijöiden kuten lehmien pötsissä, ekstrasellulaarisia polysakkarideja ja eräitä sen johdannaisia tavataan eräiden muidenkin bakteerien polysakkarideista.[3][4] Altroosi esiintyy tyypillisesti rengasrakenteisina hemiasetaaleina pyranooseina ja furanooseina. Tasapainotilassa noin 70 % altroosista on pyranooseina ja noin 30 % furanooseina.[5]

D-Altroosia valmistetaan tyypillisesti lähtemällä D-riboosista ja pidentämällä hiiliketjua käyttämällä syanohydriinejä tai nitrometaania. D-Altroosia voidaan valmistaa myös D-glukoosista käyttämällä epimerisaation katalyyttinä molybdeenihappoa.[6] L-Altroosia voidaan valmistaa L-idoosista. Toinen tapa valmistaa tätä monosakkaridia on syntetisoida sitä D-galaktoosista käyttäen Mitsunobu-reaktiota.[3]

Lähteet

  1. ↑ D-Altrose – Substance summary NCBI. Viitattu 26. lokakuuta 2012.
  2. ↑ Physical properties: D-Altrose NLM Viitattu 26.10.2012
  3. ↑ a b Nathalie Lunau & Chris Meier: Synthesis of L-Altrose and Some Derivatives. European Journal of Organic Chemistry, 2012, nro 31, s. 6260–6270. Artikkelin verkkoversio. Viitattu 26.10.2012.
  4. ↑ P.N. Hobson,C.S. Stewart: Rumen Microbial Ecosystem, s. 36. Springer, 1997. ISBN 978-0-7514-0366-4 Kirja Googlen teoshaussa (viitattu 26.10.2012). (englanniksi)
  5. ↑ Paul M. Dewick: Essentials of Organic Chemistry, s. 470. John Wiley & Sons, 2006. ISBN 978-0-470-01665-7 Kirja Googlen teoshaussa (viitattu 26.10.2012). (englanniksi)
  6. ↑ V. Bílik, I. Knĕzĕk & K. Bíliková: Reactions of saccharides catalyzed by molybdate ions XXXVII*. Preparation of D-allose and D-altrose from D-glucose. Chemical Papers, 1988, 42. vsk, nro 3, s. 401–405. Artikkelin verkkoversio. Viitattu 26.10.2012. (englanniksi)
Hiilihydraatit
Pääjoukko
Geometria
Suuri / pieni
Pentoosit
Heksoosit
Disakkaridit
Polysakkaridit
Glykosaminoglykaanit
Aminoglykosidit
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