Name: carbohydrate structure and bonding
Uploaded: 2023-04-30T18:28:47.000Z
Duration: 3 min 25 s
Channel: JoVE

K12 Standards

Florida Department of Education

High School

Life Science

SC.912.L.18

SC.912.L.18.1

Chemistry of Carbohydrates

I carboidrati sono composti cortituiti da carbonio, idrogeno e ossigeno. Queste molecole prendono il nome dalla formula empirica di molti monosaccaridi che hanno due atomi di idrogeno e un atomo di ossigeno per ogni carbonio. I carboidrati semplici sono monomeri chiamati monosaccaridi, e dimeri, detti disaccaridi.

I carboidrati complessi sono polimeri detti polisaccaridi. Un monosaccaride può essere classificato come aldoso o chetoso dal suo gruppo funzionale. Quelli che hanno un gruppo aldeidico sono detti aldosi, e quelli che hanno un gruppo chetonico sono detti chetosi.

I monosaccaridi contengono solitamente da tre a sette atomi di carbonio nelle loro catene. Ciascuno degli atomi di carbonio può essere numerato a partire dal numero uno dall'estremità più vicina al carbonio carbonilico. Gli zuccheri possono formare strutture ad anello non planari e in natura esistono principalmente in questa forma ciclica.

Le strutture ad anello si formano quando il gruppo carbonile reagisce con un gruppo idrossile all'estremità opposta della molecola, attraverso una reazione di condensazione. Il carbonio attaccato all'aldeide reattiva, o chetone, è anche definito carbonio anomerico. Queste strutture ad anello carbonio-ossigeno, possono esistere come due anomeri:alfa e beta.

Gli anomeri sono isomeri strutturali che differiscono nella configurazione del carbonio carbonile. Nella forma alfa, il gruppo idrossile sul carbonio anomerico e il gruppo CH2OH sull'ultimo carbonio all'interno dell'anello si trovano sui lati opposti dell'anello, e nella forma beta si trovano sullo stesso lato. Una convenzione di denominazione simile è usata per i legami che collegano i monosaccaridi ad altre molecole.

I legami formati sotto la struttura ad anello sono noti come collegamenti alfa, mentre quelli sopra l'anello sono noti come collegamenti beta. I numeri nel nome dei legami glicosidici indicano i numeri di carbonio dei monosaccaridi coinvolti nei legami. Quando due monosaccaridi si legano insieme attraverso legami glicosidici, formano disaccaridi.

I legami glicosidici sono legami covalenti che si formano quando il gruppo idrossile di un monosaccaride reagisce con il carbonio anomerico di un altro monosaccaride, con l'eliminazione di una molecola d'acqua. I polisaccaridi o carboidrati complessi sono una catena di monosaccaridi tenuti insieme da legami covalenti. La variazione dei legami glicosidici presenti in queste molecole può portare alla formazione di diversi tipi di polisaccaridi dallo stesso monosaccaride.

Le molecole di glucosio legate tramite legami β-1, 4-glicosidici formano la cellulosa, un polisaccaride insolubile in acqua. Le molecole di glucosio legate tramite legami α-1, 4-glicosidici formano l'amilosio, un polimero idrosolubile e un componente dell'amido. L'amido e la cellulosa sono polisaccaridi presenti nelle piante.

Il glicogeno è una molecola insolubile in acqua, composta da glucosio legata tramite legami α-1, 4-glicosidici e legami α-1, 6-glicosidici con ramificazione intermittente. Il glicogeno funge da polisaccaride di stoccaggio negli animali.

chimica dei carboidrati

I carboidrati sono una parte essenziale della dieta dell’uomo e degli animali. Cereali, frutta e verdura sono fonti naturali di carboidrati che forniscono energia al corpo, in particolare attraverso il glucosio, uno zucchero semplice che è un componente dell'amido e un ingrediente di molti alimenti di base. La formula stechiometrica (CH_2O)_n, dove n è il numero di atomi di carbonio nella molecola, rappresenta i carboidrati. In altre parole, il rapporto tra carbonio, idrogeno e ossigeno è 1:2:1 nelle molecole di carboidrati. Questa formula spiega anche l'origine del termine “carboidrato”: i componenti sono carbonio (“carbo”) e acqua (“idrato”). I carboidrati possono essere classificati in semplici e complessi. Monosaccaridi e disaccaridi sono carboidrati semplici. I polisaccaridi sono carboidrati complessi.

Monosaccaridi

I monosaccaridi sono zuccheri semplici, il più comune dei quali è il glucosio. Nei monosaccaridi, il numero di atomi di carbonio varia solitamente da tre a sette. Se lo zucchero ha un gruppo aldeidico (il gruppo funzionale con la struttura R-CHO), è un aldoso, e se ha un gruppo chetonico (il gruppo funzionale con la struttura RC(=O)R'), è un chetoso. A seconda del numero di atomi di carbonio nello zucchero, possono essere triosi (tre atomi di carbonio), pentosi (cinque atomi di carbonio) e/o esosi (sei atomi di carbonio).

Galattosio e fruttosio sono altri monosaccaridi comuni. Glucosio, galattosio e fruttosio sono monosaccaridi isomerici (esosi), nel senso che hanno la stessa formula chimica ma le loro strutture sono leggermente diverse. Il glucosio e il galattosio sono aldosi, mentre il fruttosio è un chetosio.

I monosaccaridi possono esistere come una catena lineare o come molecole a forma di anello. Nelle soluzioni acquose, solitamente hanno forma di anelli. Il glucosio in forma di anello può avere due diverse disposizioni dei gruppi idrossilici (OH) attorno al carbonio anomerico (carbonio 1 che diventa asimmetrico nel processo di formazione dell'anello). Se nello zucchero il gruppo idrossile è al di sotto del numero di carbonio 1, è nella posizione alfa (α) e se è sopra il piano, è nella posizione beta (β).

Disaccaridi

I disaccaridi si formano quando due monosaccaridi subiscono una reazione di disidratazione (o una reazione di condensazione o sintesi di disidratazione). Durante questo processo, il gruppo idrossile di un monosaccaride si combina con l'idrogeno di un altro monosaccaride, rilasciando una molecola d'acqua e formando un legame covalente. Questo è chiamato legame glicosidico. I legami glicosidici possono essere di tipo alfa o beta. Un legame alfa si forma quando il gruppo OH sul carbonio-1 del primo glucosio è sotto il piano dell'anello, mentre si forma un legame beta quando il gruppo OH sul carbonio-1 è sopra il piano dell'anello. Il disaccaride più comune è il saccarosio, o zucchero da tavola, composto da monomeri di glucosio e fruttosio.

Polisaccaridi

Una lunga catena di monosaccaridi legati da legami glicosidici è un polisaccaride. La catena può essere ramificata oppure no e può contenere diversi tipi di monosaccaridi. Il peso molecolare può essere di 100.000 dalton o più a seconda del numero di monomeri uniti. Amido, glicogeno, cellulosa e chitina sono esempi di polisaccaridi.

Le piante immagazzinano l'amido sotto forma di zuccheri. Nelle piante, questi zuccheri sono costituiti da una miscela di amilosio e amilopectina (entrambi polimeri del glucosio). L'amido comprende monomeri di glucosio uniti da legami glicosidici α 1-4 o α 1-6. I numeri 1-4 e 1-6 si riferiscono al numero di carbonio dei due residui che si sono uniti per formare il legame.

Il glicogeno è la forma di conservazione del glucosio negli esseri umani e in altri vertebrati ed è composto da monomeri di glucosio. Il glicogeno è l'equivalente animale dell'amido ed è una molecola altamente ramificata solitamente immagazzinata nelle cellule del fegato e dei muscoli. Ogni volta che i livelli di glucosio nel sangue diminuiscono, il glicogeno si scompone per rilasciare glucosio.

La cellulosa è il biopolimero naturale più abbondante. La cellulosa comprende principalmente la parete cellulare di una pianta. Ciò fornisce il supporto strutturale della cellula. Il legno e la carta sono per la maggior parte di natura cellulosica. I monomeri di glucosio comprendono la cellulosa che si collega con legami glicosidici β 1-4

Questo testo è adattato da <a href="https://openstax.org/books/biology-2e/pages/3-2-carbohydrates">Openstax, Biology 2e, Chapter 3.4: Carbohydrates.</a>

Chimica dei carboidrati

I carboidrati sono una parte essenziale della dieta nell'uomo e negli animali. Cereali, frutta e verdura sono fonti naturali di carboidrati che forniscono ...

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SC.912.L.18.7

A. All living things are composed of four basic categories of macromolecules and share the same basic needs for life.

B. Living organisms acquire the energy they need for life processes through various metabolic pathways (primarily photosynthesis and cellular respiration).

C. Chemical reactions in living things follow basic rules of chemistry and are usually regulated by enzymes.

D. The unique chemical properties of carbon and water make life on Earth possible.

Carbohydrate Structure and Bonding

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