Skip to main content
Ch.6 Carbohydrates–Life’s Sweet Molecules
Chapter 3, Problem 6.31

Pentoses also exist in a ring form, but they most commonly occur as furanose rings. d-Ribose exists in its furanose ring form in the nucleic acid RNA. Using the structure of d-ribose from Table 6.1, draw the furanose form of ß-d-ribose.

Verified step by step guidance
1
Identify the linear structure of d-ribose, which is an aldopentose with five carbon atoms and an aldehyde group at the first carbon.
Recognize that in the furanose form, d-ribose forms a five-membered ring, which includes four carbon atoms and one oxygen atom.
To form the furanose ring, the hydroxyl group on the C-4 carbon attacks the aldehyde group on the C-1 carbon, creating a hemiacetal linkage.
In the ß-anomer of d-ribose, the newly formed hydroxyl group on the C-1 carbon (anomeric carbon) is positioned above the plane of the ring, which is the ß-configuration.
Draw the five-membered ring structure, ensuring that the oxygen atom is part of the ring and the ß-hydroxyl group is above the plane at the anomeric carbon.

Verified Solution

Video duration:
6m
This video solution was recommended by our tutors as helpful for the problem above.
Was this helpful?

Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Furanose Structure

Furanose refers to a five-membered ring structure formed by the cyclization of pentose sugars, such as d-ribose. In this configuration, one of the carbons in the sugar forms a bond with the oxygen atom, creating a stable ring. This structure is significant in biochemistry, particularly in the formation of nucleotides and nucleic acids.
Recommended video:
Guided course
1:01
Structural Formula Concept 2

d-Ribose

d-Ribose is a naturally occurring sugar that is a crucial component of RNA (ribonucleic acid). It is a pentose sugar, meaning it contains five carbon atoms, and plays a vital role in cellular metabolism and energy production. Understanding its structure and function is essential for grasping how genetic information is stored and transmitted in living organisms.
Recommended video:
Guided course
1:30
D vs L Enantiomers Concept 1

Beta Anomer

The term 'beta' in carbohydrate chemistry refers to the configuration of the hydroxyl group on the anomeric carbon in a cyclic sugar. In the case of ß-d-ribose, the hydroxyl group on the anomeric carbon (C1) is positioned above the plane of the ring. This distinction is important for understanding the reactivity and interactions of sugars in biological systems.
Recommended video:
Guided course
01:26
Beta Decay Example 1