Oligosaccharider

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Oligosaccharider  (fra græsk ὀλίγος  - få) er kulhydrater, der indeholder fra 2 til 10 monosacchariderester .

Oligosaccharider, der består af de samme monosaccharider, kaldes homoligosaccharider, og de, der består af forskellige monosaccharider, kaldes heterooligosaccharider.

De mest almindelige af oligosacchariderne er disaccharider og trisaccharider . Af kemisk natur er disaccharider O-glykosider (acetaler), hvor det andet monosaccharidmolekyle fungerer som en aglycon. Afhængigt af strukturen er disaccharider opdelt i to grupper: reducerende og ikke-reducerende.

Klassificering af oligosaccharider

Den strenge nomenklatur af oligosaccharider er meget besværlig. Navnet på oligosaccharidet er dannet i overensstemmelse med typen af ​​O-substituerede derivater af monosaccharider, baseret på navnet på den reducerende enhed, hvilket angiver alle tilgængelige substituenter; for ikke-reducerende oligosaccharider svarer nomenklaturen til glycosiders. Navnene på lineære oligosaccharider bruger ofte en sekventiel opregning af monosaccharidrester med en indikation af typen af ​​forbindelse mellem dem.

1. Disaccharider (dioser) C 12 H 22 O 11

Strukturel formel	Trivielt navn	Systematisk navn
	Trehalulose	a-D-glucopyranosyl-(1,1)-D-fructose (3S,4R,5R)-3,4,5,6-tetrahydroxy-1-[(2S,3R,4S,5S, 6R)-3, 4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexan-2-on
	saccharose (saccharose)	α-D-glucopyranosyl-(1,2)-β-D-fructofuranose (2R,3R,4S,5S,6R)​-​2-​[​(2S,3S,4S,5R)​-​3, 4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-6-(hydroxymethyl)oxan-3,4,5-triol
	turanosa	a-D-glucopyranosyl-(1,3)-D-fructose ​(3S,4R,5R)​-1,2,4,5-tetrahydroxy-3-[(2R,3R,4S,5S,6R)- 3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexan-2-on
	Maltulose	a-D-glucopyranosyl-(1,4)-D-fructose (3S,4R,5R)-1,3,5,6-tetrahydroxy-4-[(2R,3R,4S,5S,6R)-3, 4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexan-2-on
	lucrose	a-D-glucopyranosyl-(1,5)-D-fructose (3S,4R,5R)-1,3,4,6-tetrahydroxy-5-[(2R,3R,4S,5S,6R)-3, 4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexan-2-on
	Isomaltulose (palatinose)	a-D-glucopyranosyl-(1,6)-D-fructose (3S,4R,5R)-1,3,4,5-tetrahydroxy-6-[(2R,3R,4S,5S,6R)-3, 4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexan-2-on
	Trehalose (mykose)	1-O-α-D-glucopyranosyl-D-glucose α-D-glucopyranosyl-(1,1)-α-D-glucopyranose (α,α-trehalose) (2R,3R,4S,5S,6R) ​1-​[​(2R,3R,4S,5S,6R)-​-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-(hydroxymethyl)oxan-3, 4,5-triol α-D-glucopyranosyl-(1,1)-β-D-glucopyranose (α,β-trehalose, neotrehalose) β-D-glucopyranosyl-(1,1)-β-D-glucopyranose (β ,β-trehalose)
	Coyibiose	a-D-glucopyranosyl-(1,2)-D-glucose (2R,3S,4R,5R)-3,4,5,6-tetrahydroxy-2-[(2R,3R,4S,5S,6R)- 3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexanal
	soforose	2-O-β-D-glucopyranosyl-D-glucose β-D-glucopyranosyl-(1,2)-α-D-glucopyranose (α-sophorose) β-D-glucopyranosyl-(1,2)-β-D -glucopyranose (β-sophorose)
	Nigerose (seikbiose)	a-D-glucopyranosyl-(1,3)-a-D-glucopyranose
	Laminaribiose	β-D-glucopyranosyl-(1,3)-a-D-glucopyranose
	Maltose	α-D-glucopyranosyl-(1,4)-α-D-glucopyranose 4-O-α-D-glucopyranosyl-D-glucose (α-maltose) α-D-glucopyranosyl-(1-4)-β-D -glucopyranose 4-O-β-D-glucopyranosyl-D-glucose (β-maltose)
	Cellobiose (Cellose)	4-O-β-D-glucopyranosyl-D-glucose β-D-glucopyranosyl-(1,4)-α-D-glucopyranose (α-cellobiose) β-D-glucopyranosyl-(1,4)-β-D-glucopyranose (β-cellobiose)
	Isomaltose	a-D-glucopyranosyl-(1,6)-a-D-glucopyranose
	Gentiobiose (amygdalose)	β-D-glucopyranosyl-(1,6)-α-D-glucopyranose (α-gentiobiose) β-D-glucopyranosyl-(1,6)-β-D-glucopyranose (β-gentiobiose)
	Lactose (lactobiose, tabletose)	4-O-β-D-galactopyranosyl-D-glucose, β-D-galactopyranosyl-(1,4)-α-D-glucopyranose (α-lactose) β-D-galactopyranosyl-(1,4)-β-D-glucopyranose (β-lactose)
	allolactose	β-D-galactopyranosyl (1,6)-β-D-glucopyranose
	melibiosa	a-D-galactopyranosyl (1,6)-D-glucose
	2a-Mannobiose	a-D-mannopyranosyl-(1,2)-a-D-mannopyranose, 2-O-a-D-mannopyranosyl-D-mannose
	3a-Mannobiose	a-D-mannopyranosyl-(1,3)-a-D-mannopyranose, 3-O-a-D-mannopyranosyl-D-mannose
	Inulobiose	β-D-fructofuranosyl-(2,1)-β-D-fructofuranose
	Levanbiosa	β-D-fructofuranosyl-(2,6)-β-D-fructofuranose
	Lactulose	β-D-galactopyranosyl-(1,4)-β-D-fructofuranose (2S,3R,4S,5R,6R)-2-[(2R,3S,4S,5R)-4,5-dihydroxy-2, 5-bis(hydroxymethyl)oxolan-3-yl]oxy-6-(hydroxymethyl)oxan-3,4,5-triol
	Melibiuosa	a-D-galactopyranosyl-(1,6)-D-fructose
	Vicyanose	a-D-arabinopyranosyl-(1,6)-D-glucopyranose
	Sambubiose	α-D-xylofuranosyl-(1,2)-β-D-glucopyranose
	Robinose (robinobiose)	α-D-rhamnopyranosyl-(1,6)-β-D-galactopyranose
	Rutinosa	α-L-rhamnopyranosyl-(1,6)-β-D-glucopyranose
	Neohesperidose	α-L-rhamnopyranosyl-(1,2)-β-D-glucopyranose

2. Trisaccharider (trioser) C 18 H 32 O 16

Strukturel formel	Trivielt navn	Systematisk navn
	Raffinose (raffinose, 6G-α-D-galactosylsaccharose)	α-D-galactopyranosyl-(1,6)-α-D-glucopyranosyl-(1,2)-β-D-fructofuranose ​(2R,3R,4S,5S,6R)​-​2-​[​( 2S,3S,4S,5R)-​3,4-​dihydroxy-​2,5-​bis​(hydroxymethyl)​oxolan-​​2-​yl]oxy-​6-​[ [​(2S, 3R,4S,5R,6R)​3,4,5-​trihydroxy-​6-​(hydroxymethyl)​oxan-​​2-​yl]oxymethyl]oxan-​3,4,5-​triol
	melicytose	α-D-glucopyranosyl-(1,3)-β-D-fructofuranosyl-(2,1)-α-D-glucopyranose
	Maltotriose	α-D-glucopyranosyl-(1,4)-α-D-glucopyranosyl-(1,4)-α-D-glucopyranose
	isomaltotriose	α-D-glucopyranosyl-(1,6)-α-D-glucopyranosyl-(1,6)-α-D-glucopyranose
	gentianose	β-D-glucopyranosyl-(1,6)-α-D-glucopyranosyl-(1,2)-β-D-fructofuranosid
	Solatriosa	α-L-rhamnopyranosyl-(1,2)-[β-D-glucopyranosyl-(1,3)]-D-galactose
	Cellotriose	β-D-glucopyranosyl-(1,4)-β-D-glucopyranosyl-(1,4)-D-glucopyranose
	Erloza (glycosylsaccharose, 4G-α-D-glucopyranosylsaccharose)	α-D-glucopyranosyl-(1,4)-α-D-glucopyranosyl-(1,2)-β-D-fructofuranose
	Panosa	α-D-glucopyranosyl-(1,6)-α-D-glucopyranosyl-(1,4)-α-D-fructofuranose
	Nigerotriasis	α-D-glucopyranosyl-(1,3)-α-D-glucopyranosyl-(1,3)-α-D-glucopyranose
	1-Kestose (1F-β-D-fructosylsaccharose, 1F-kestotriose, isokestose))	β-D-fructofuranosyl-(2,1)-β-D-fructofuranosyl-(1,2)-α-D-glucopyranose (2R,3R,4S,5S,6R)-2-[(2S,3S,4S) ,5R)-2-[[(2R,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-( hydroxymethyl)oxolan-2-yl]oxy-6-(hydroxymethyl)oxan-3,4,5-triol
	6-Kestose (6F-β-D-fructosylsaccharose, 6F-kestotriose)	β-D-fructofuranosyl-(2,6)-β-D-fructofuranosyl-(1,2)-α-D-glucopyranose
	Neokestose (6G-β-D-fructosylsaccharose, 6G-kestotriose)	1,6-bis(β-D-fructofuranosyl)-a-D-glucopyranose
	Inulotriose (fructotriose)	β-D-fructofuranosyl-(2,1)-β-D-fructofuranosyl-(2.1)-β-D-fructofuranose
	2-fucosyllactose	α-L-fucopyranosyl-(1,2)-β-D-galactopyranosyl-(1.4)-D-glucopyranose
	3-fucosyllactose	α-L-fucopyranosyl-(1,3)-[β-D-galactopyranosyl-(1.4)]-D-glucopyranose
	Mannotriose	α-D-mannopyranosyl-(1,4)-α-D-mannopyranosyl-(1,4)-α-D-mannopyranose
	Dextrantriose	a-D-glucopyranosyl-(1,6)-a-D-glucopyranosyl-(1,6)-glucose
	levantriose	β-D-fructofuranosyl-(2,6)-β-D-fructofuranosyl-(2,6)-β-D-fructofuranose
	Inulotriose	β-D-fructofuranosyl-(2,1)-β-D-fructofuranosyl-(2,1)-β-D-fructofuranose
	Theanderosa	a-D-glucopyranosyl-(1,6)-a-D-glucopyranosyl-(1,2)-fructose
	D-rhamninosa	6-O-[3-O-(α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]-D-galactose

3. Tetrasaccharider (tetraoser) C 24 H 42 O 21

Strukturel formel	Trivielt navn	Systematisk navn
	Stachyose (mannotetrose, digalactosylsaccharose))	α-D-galactopyranosyl-(1,6)-α-D-galactopyranosyl-(1,6)-α-D-glucopyranosyl-(1,2)-β-D-fructofuranosid
	Lichiose	α-D-galactopyranosyl-(1,6)-α-D-glucopyranosyl-(1,2)-β-D-fructofuranosyl-(1,1)-α-D-galactopyranosid
	Isolichiosis	α-D-galactopyranosyl-(1,6)-α-D-glucopyranosyl-(1,2)-β-D-fructofuranosyl-(3,1)-α-D-galactopyranosid
	Sesamosa	α-D-glucopyranosyl-(1,2)-β-D-fructofuranosyl-(6,1)-α-D-galactopyranosyl-(6,1)-α-D-galactopyranosid
	Cellotetraose	β-D-glucopyranosyl-(1,4)-β-D-glucopyranosyl-(1,4)-β-D-glucopyranosyl-(1,4)-D-galactopyranose
	Nystose (1,1-kestotetraose)	β-D-fructofuranosyl-(2,1)-β-D-fructofuranosyl-(2.1)-β-D-fructofuranosyl-(1,2)-α-D-glucopyranose
	Bifurcose (1,6-kestotetraose)	1,6-bis-(β-D-fructofuranosyl)-β-D-fructofuranosyl-(2,1)-α-D-glucopyranose
	Maltotetraose	α-D-glucopyranosyl-(1,4)-α-D-glucopyranosyl-(1,4)-α-D-glucopyranosyl-(1,4)-α-D-glucopyranose
	Isomaltotetraose	α-D-glucopyranosyl-(1,6)-α-D-glucopyranosyl-(1,6)-α-D-glucopyranosyl-(1,6)-α-D-glucopyranose
	Inulotetraose (fruktotetraose)	β-D-fructofuranosyl-(2,1)-β-D-fructofuranosyl-(2,1)-β-D-fructofuranosyl-(2.1)-β-D-fructofuranose
	Levantetraosa	β-D-fructofuranosyl-(2,6)-β-D-fructofuranosyl-(2,6)-β-D-fructofuranosyl-(2,6)-β-D-fructofuranose

4. Pentasaccharider (pentaose) C 30 H 52 O 26

Strukturel formel	Trivielt navn	Systematisk navn
	1,1,1-Kestopentose (fruktosylnistose)	β-D-fructofuranosyl-(2,1)-β-D-fructofuranosyl-(2,1)-β-D-fructofuranosyl-(2,1)-β-D-fructofuranosyl-(1,2)-α- D-glucopyranose
	Maltopentaose	α-D-glucopyranosyl-(1,4)-α-D-glucopyranosyl-(1,4)-α-D-glucopyranosyl-(1,4)-α-D-glucopyranosyl-(1,4)-α- D-glucopyranose
	cellopentaose	β-D-glucopyranosyl-(1,4)-β-D-glucopyranosyl-(1,4)-β-D-glucopyranosyl-(1,4)-β-D-glucopyranosyl-(1,4)-D- galactopyranose
	Verbascose (trigalactosylsaccharose)	α-D-galactopyranosyl-(1,6)-α-D-galactopyranosyl-(1,6)-α-D-galactopyranosyl-(1,6)-α-D-glucopyranosyl-(1,2)-β- D-fructofuranose

5. Hexasaccharider (hexaoser) C 36 H 62 O 31

Strukturel formel	Trivielt navn	Systematisk navn
	Maltohexaose	α-D-glucopyranosyl-(1,4)-α-D-glucopyranosyl-(1,4)-α-D-glucopyranosyl-(1,4)-α-D-glucopyranosyl-(1,4)-α- D-glucopyranosyl-(1,4)-a-D-glucopyranose
	Cellohexaose	β-D-glucopyranosyl-(1,4)-β-D-glucopyranosyl-(1,4)-β-D-glucopyranosyl-(1,4)-β-D-glucopyranosyl-(1,4)-β- D-glucopyranosyl-(1,4)-D-galactopyranose

6. Heptasaccharider (heptaoser) C 42 H 72 O 36

Strukturel formel	Trivielt navn	Systematisk navn
	Celloheptaose	β-D-glucopyranosyl-(1,4)-β-D-glucopyranosyl-(1,4)-β-D-glucopyranosyl-(1,4)-β-D-glucopyranosyl-(1,4)-β- D-glucopyranosyl-(1,4)-β-D-glucopyranosyl-(1,4)-D-galactopyranose

Homooligosaccharider

Disakkarider:

• Maltose
• Cellobiose
• nigerosa
• Rutinosa
• turanosa
• Gentiobiose
• Trehalose
• melibiosa

Trisaccharider:

• Rafinose
• gentianose
• melicytose
• Maltotriose
• Erloz

Tetrasaccharider:

• Stachyose

Pentasaccharider:

• Maltopentoza

Hexasaccharider:

• Maltohexose

Heterooligosaccharider

Disakkarider:

• saccharose
• Laktose

Fysiske egenskaber

Mange oligosaccharider er krystallinske faste stoffer eller ikke-krystalliserende sirupper, hvide eller farveløse, meget opløselige i vand , tungtopløselige i lavere alkoholer og praktisk talt uopløselige i andre almindelige opløsningsmidler, med undtagelse af dimethylformamid , formamid og dimethylsulfoxid . Ved forhøjede temperaturer er de lavere oligosaccharider opløselige i eddikesyre og pyridin . Nogle højere uforgrenede regulære oligosaccharider såsom cellodextriner er vanskelige at opløse i vand, og deres opløselighed falder hurtigt med stigende molekylvægt. Mange oligosaccharider har en sød smag [1] .

At være i naturen

I den frie stat er oligosaccharider mest udbredt i planteverdenen , hvor de tilsyneladende primært spiller rollen som reservekulhydrater . De karakteristiske og mest almindelige repræsentanter for planteoligosaccharider er oligosaccharider af saccharosegruppen : melicitose , raffinose , gentianose , stachyose osv.

Ansøgning

Nogle oligosaccharider, såsom saccharose , er af stor praktisk betydning, og med hensyn til årlig produktion (over 100 millioner tons) indtager de en af ​​de første pladser blandt individuelle organiske forbindelser . Lactose og cyclodextriner produceres i små mængder og bruges i medicinalindustrien .

Noter

1. ↑ H. K. Kochetkov , A. F. Bochkov, B. A. Dmitriev, A. I. Usov O. S. Chizhov, V. N. Shibaev. Kemi af kulhydrater. — M .: Kemi, 1967. — 674 s.

Tematiske steder	FMA
Ordbøger og encyklopædier	Fantastisk catalansk Stor russer Britannica (online) Brockhaus
I bibliografiske kataloger	NDL : 00568928 NKC : ph123728

Multisaccharider
disaccharider	saccharose Laktose Maltose nigerosa Trehalose turanosa Cellobiose melibiosa Gentiobiose Vicyanose Rutinosa Isomaltose cayibiosa Inulobiose Isomaltulose Lactulose Laminaribiose lucrose Maltulose Robinose soforose Trehalulose 3a-Mannobiose allolactose Melibiulose
Trisaccharider	Rafinose melicytose Maltotriose isomaltotriose gentianose Solatriosa Cellotriose Erloz Panosa 1-Kestoza 6-Kestoza Inulotriose Fucosyllactose Mannotriose Neokestose
Tetrasaccharider	Acarbose Stachyose Nystose Maltotetraose Fructosylnistose Inulotetraose Rhamninose
Pentasaccharider	Maltopentoza Verbascose
Hexasaccharider	Maltohexose
Oligosaccharider	Fruktooligosaccharider Galactooligosaccharider Mannanoligosaccharider Isomaltanoligosaccharider Maltodextrin
Polysaccharider	Glykogen Stivelse Cellulose Chitin amylose Amylopectin Sahylose Fruktaner ( inulin , levan ) Dextran Dextrin Pektin Galactan Mannan Xylan Araban Galactomannan Agarose Lichenin Pullulan

Kulhydrater
Generel:	Aldoses ketose Furanoser pyranoser
Geometri	Anomerer Mutarotation Haworth projektion
Monosaccharider	Dioses Aldodiose ( glycoladehyd ) Trioser Ketotriose ( dihydroxyacetone ) Aldotriose ( glyceraldehyd ) tetroser Ketotetroza ( Erythrulose ) Altotetroser ( Erythrose , Threose ) Pentoser Ketopentoser ( ribulose , xylulose ) Aldopentoser ( Ribose , Arabinose , Xylose , Lyxose , Apiose ) Deoxysaccharider ( Deoxyribose ) Hexoser Ketohexoser ( Psicose , Fructose , Sorbose , Tagatose ) Aldohexoser ( Allose , Altrose , Glucose , Mannose , Gulose , Idose , Galactose , Talose ) Deoxysaccharider ( Fucose , Fuculose , Rhamnose ) Heptoser Ketoheptoser ( Sedoheptulose , Mannoheptulose ) >7 Oktoser Nonose ( neuraminsyre ) Sialinsyrer ( N-acetylneuraminsyre )
Multisaccharider	disaccharider Trisaccharider Tetrasaccharider Pentasaccharider Hexasaccharider Oligosaccharider Polysaccharider ( glycaner , glucaner , fructaner )
Derivater af kulhydrater	Amino sukker Fosfosukker anhydrosukker Glykosider N-glycosider Glikali Glykoner enoser Glycoseiner Glykosaner Ozon Osazoner Glycosaminoglycaner Heparin Heparinsulfat Chondroitin Chondroitinsulfat Hyaluronsyre Geparan Dermatan Dermantansulfat Keratan Keratansulfat Peptidoglycan Chitosamin Chondrosamin Aminoglykosider Kanamycin Streptomycin Tobramycin Neomycin Paromomycin Apramycin Gentamicin Netilmicin Amikacin