Sorbose is a stereoisomer of the sugar fructose. Its sweetne…
Sorbose is a stereoisomer of the sugar fructose. Its sweetness is similar to that of table sugar and it is used in the commercial production of Vitamin C. One enantiomer of sorbose, namely D‑sorbose, is shown below. D‑sorbose can exist in an open chain form (D‑sorbose) or it can cyclize to form a six-membered ring (α‑D‑sorbopyranose). Answer the questions below about D‑sorbose and α‑D‑sorbopyranose. Which of the Fischer projections (A-F) below represent D‑sorbose? [Fischer] Which of the chair conformations (T-Z) below represent the MOST stable conformation of α‑L‑sorbopyranose? [Mchair] Which of the chair conformations (T-Z) below represent the LEAST stable conformation of α‑L‑sorbopyranose? [Lchair] How many total stereoisomers are possible for α‑D‑sorbopyranose (including the one drawn)? [stereopyr] How many diastereomers are possible for D‑sorbose? [diassor] The anomeric center of a cyclic sugar is the newly formed chiral center resulting from the cyclization reaction. Which of the carbon atoms labeled 1-6 above is the anomeric center? [anomeric] Identify ONE chair conformation (T-Z) that represents the enantiomer of α‑D‑sorbopyranose. [enantiomer] What is the relationship between the Fischer projections labeled C and F? [relationship]
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