In water, D-glucose mainly occupies cyclic forms. The C5 hydroxy group adds to the C1 aldehyde, forming a cyclic hemiacetal; reversible opening restores the aldehyde. Reclosure can give either anomer. Their changing proportions cause mutarotation, the approach of optical rotation to an equilibrium value. This pathway involves changing chemical bonds, rather than simply rotating a hydroxy group about a single chemical bond.[ref]
Figure 1.
Two D-glucose anomers connect through the same open-chain aldose
. Original Haworth projections share an open-chain Fischer projection. Both rings have the C5 group up and C2/C3/C4 hydroxy groups down/up/down. The C1 hydroxy group is down in alpha-D-glucopyranose and up in beta-D-glucopyranose. Ring carbon-hydrogen chemical bonds are omitted. Arrows indicate reversible connectivity, not measured reaction rates or relative populations. The Haworth projection is symbolic; actual rings are puckered. Details.
In this conventional Haworth projection, C5's group points up. The alpha anomer's C1 hydroxy group points down, on the opposite face; the beta anomer's points up, on the same face. C2/C3/C4 retain down/up/down hydroxy groups. These are above/below relationships to a reference ring plane, not a claim that the ring is physically flat.[ref]
The anomeric carbon is C1, the existing carbonyl group carbon that becomes a new stereocenter; no extra carbon chemical atom appears. The two anomers differ at that centre while retaining the other configurations.[ref]
Trace the ring as C1–C2–C3–C4–C5–O5–C1, where O5 denotes the oxygen originally in the C5 hydroxy group. It contains five carbon chemical atoms and one oxygen; C6 remains attached outside the ring. The C1 carbonyl group oxygen becomes the C1 hydroxy group oxygen. This accounts for every oxygen: O5 in the ring and five hydroxy groups at C1, C2, C3, C4 and C6. Ring closure preserves . A six-membered ring and a six-carbon sugar are thus different counts.