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Topic: Why are disaccharides stable?  (Read 2255 times)

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Offline tdod

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Why are disaccharides stable?
« on: April 04, 2013, 08:37:58 PM »
B/c the glycosidic bond b/w two sugar monomers turns the anomeric carbon into an acetal, shouldn't it the disaccharide be highly unstable and therefore immediately hydrolyze back into monomers? Obviously, this is not the case... but I'd really appreciate if someone could explain why.

Thanks!.

Offline Dan

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Re: Why are disaccharides stable?
« Reply #1 on: April 05, 2013, 03:23:35 AM »
B/c the glycosidic bond b/w two sugar monomers turns the anomeric carbon into an acetal, shouldn't it the disaccharide be highly unstable and therefore immediately hydrolyze back into monomers?

Your question seems to arise from the assumption that acetals are highly unstable. What makes you think that is true?
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Offline Babcock_Hall

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Re: Why are disaccharides stable?
« Reply #2 on: April 05, 2013, 09:27:21 AM »
It might be helpful if you clarify one thing.  Are we talking about thermodynamics (stable versus unstable), or are we talking kinetics (labile versus inert)?

Offline Dean

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Re: Why are disaccharides stable?
« Reply #3 on: April 07, 2013, 01:55:15 PM »
An interesting question. I'll try to find the answer. ::)

Offline Babcock_Hall

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Re: Why are disaccharides stable?
« Reply #4 on: April 08, 2013, 10:12:02 AM »
An interesting question. I'll try to find the answer. ::)
Is that directed to the OP or to me?  If it is directed to me, then I would note that the language used by the OP points in both directions (kinetics and thermodynamics).  Biochemists typically divide bonds into two kinds (high-energy and low-energy), based upon how negative the free energies of hydrolysis at pH 7 (sometimes given the symbol ΔG') are.  The line in the sand is arbitrary, but one textbook draws it at -25 kJ/mol at 25 °C IIRC.  The disaccharides I have looked up fall into both categories, depending on particulars.

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