25.6 Cyclic Forms of Carbohydrates: Furanose Forms

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1 .6 Cyclic Forms of Carbohydrates: Furanose Forms

2 Recall from Section 7.8 R R' C + R" Product is a hemiacetal. R" C R R'

3 R C Cyclic emiacetals R C Aldehydes and ketones that contain an group elsewhere in the molecule can undergo intramolecular hemiacetal formation. The equilibrium favors the cyclic hemiacetal if the ring is - or 6-membered. 6

4 Carbohydrates Form Cyclic emiacetals C C equilibrium lies far to the right cyclic hemiacetals that have -membered rings are called furanose forms

5 D-Erythrose C C stereochemistry is maintained during cyclic hemiacetal formation

6 D-Erythrose

7 D-Erythrose turn 90

8 D-Erythrose move into position by rotating about bond between carbon- and carbon-

9 D-Erythrose

10 D-Erythrose close ring by hemiacetal formation between at C- and carbonyl group

11 D-Erythrose

12 C C D-Erythrose stereochemistry is variable at anomeric carbon; two diastereomers are formed anomeric carbon

13 D-Erythrose α-d-erythrofuranose β-d-erythrofuranose

14 D-Ribose C C furanose ring formation involves group at C-C

15 D-Ribose C C C C need C()-C() C() bond rotation to put in proper orientation to close -membered ring

16 D-Ribose C C C C

17 D-Ribose C C C group becomes a substituent on ring

18 D-Ribose C C C β-d-ribofuranose C group becomes a substituent on ring

19 .7 Cyclic Forms of Carbohydrates: Pyranose Forms

20 Carbohydrates Form Cyclic emiacetals C C cyclic hemiacetals that have 6-membered 6 rings are called pyranose forms

21 D-Ribose C C pyranose ring formation involves group at C-C

22 D-Ribose C C C C pyranose ring formation involves group at C-C

23 D-Ribose C C pyranose ring formation involves group at C-C

24 D-Ribose C C β-d-ribopyranose

25 D-Ribose α-d-ribopyranose

26 D-Glucose C 6 C pyranose ring formation involves group at C-C

27 D-Glucose 6 C C 6 C C pyranose ring formation involves group at C-C

28 D-Glucose 6 C C need C()-C() C() bond rotation to put in proper orientation to close 6-membered 6 ring

29 D-Glucose C 6 C 6 C C need C()-C() C() bond rotation to put in proper orientation to close 6-membered 6 ring

30 D-Glucose Glucose C C C C 6 β-d-glucopyranose Glucopyranose C C 6

31 D-Glucose Glucose β-d-glucopyranose Glucopyranose C C 6 α-d-glucopyranose Glucopyranose C C 6

32 D-Glucose 6 C β-d-glucopyranose pyranose forms of carbohydrates adopt chair conformations

33 D-Glucose 6 C C 6 β-d-glucopyranose all substituents are equatorial in β-d-glucopyranose

34 D-Glucose C C β-d-glucopyranose α-d-glucopyranose group at anomeric carbon is axial in α-d-glucopyranose

35 Figure. C C Less than % of the open-chain form of D-ribose is present at equilibrium in aqueous solution.

36 Figure. 76% of the D-ribose is a mixture of the α and β- pyranose forms, with the β-form predominating β-d-ribopyranose (6%) α-d-ribopyranose (0%)

37 Figure. The α and β-furanose forms comprise % of the mixture. C C β-d-ribofuranose (8%) α-d-ribofuranose (6%)

38 .8 Mutarotation

39 Mutarotation Mutarotation is a term given to the change in the observed optical rotation of a substance with time. Glucose, for example, can be obtained in either its α or β-pyranose form. The two forms have different physical properties such as melting point and optical rotation. When either form is dissolved in water, its initial rotation changes with time. Eventually both solutions have the same rotation.

40 Mutarotation of D-Glucose C C β-d-glucopyranose α-d-glucopyranose Initial: [α][ D +8.7 Initial: [α][ D +.

41 Mutarotation of D-Glucose C C β-d-glucopyranose α-d-glucopyranose Initial: [α][ D +8.7 Initial: [α][ D +. Final: [α][ D +.

42 Mutarotation of D-Glucose C C β-d-glucopyranose α-d-glucopyranose Initial: [α][ D +8.7 Initial: [α][ D +. Final: [α][ D +.

43 Mutarotation of D-Glucose C C β-d-glucopyranose α-d-glucopyranose Explanation: After being dissolved in water, the α and β forms slowly interconvert via the open- chain form. An equilibrium state is reached that contains 6% β and 6% α.

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