Thursday 10 December 2015

organic chemistry - Why does the fructose monomer in sucrose appear different from isolated fructose?


I understood that the representation of fructose is:


enter image description here


But during the formation of sucrose:


enter image description here


How did fructose, whose representation is given in the first picture, turn out to be different in the second. I tried to visualize myself rotating the molecule but the position of oxygen changes and it doesn't match with the one in sucrose.



Answer



Ah, a (fairly) common conundrum that assails us Chemistry students when we start Biochem. ;-)


At first glance, the fructose molecule in your first picture, and that in the second picture appear to have different conformations:




enter image description here enter image description here



Believe me, they're the same. "How?" you ask? Stay with me here (it requires a little imagination):


Draw a vertical line/axis on your first diagram along the plane of the furanose ring, connecting the oxygen atom at the apex, right down to the middle of the C3-C4 bond. Then rotate the molecule 180 degrees counter-clockwise.


Now compare this with the fructose residue in sucrose.


(I lack the necessary Org. Chem. sketching tools to depict this... apologies)




If you weren't able to wrap your head around "rotation" bit, then, let's assign locant numbers to the carbon atoms in the two diagrams and then compare them:




enter image description here enter image description here


I've drawn them tiny, my bad



Must've clicked by now ;)


No comments:

Post a Comment

readings - Appending 内 to a company name is read ない or うち?

For example, if I say マイクロソフト内のパートナーシップは強いです, is the 内 here read as うち or ない? Answer 「内」 in the form: 「Proper Noun + 内」 is always read 「ない...