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Draw the following monosaccharides, using chair conformations for the pyranoses and Haworth projections for the furanoses.

(a)Dmannopyranose(C2epimerofglucose)(b)Dgalactopyranose(C4epimerofglucose)(c)Dallopyranose(C3epimerofglucose)(d)Darabinofuranose(e)Dribofuranose(C2epimerofarabinose)

Short Answer

Expert verified

(a)

Dmannopyranose

(b)

Dgalactopyranose

(c)

Dallopyranose

(d)

Darabinofurinose

(e)

Dribofuranose

Step by step solution

01

Pyranose, furanose, Epimers and Anomers

Pyranose is a six-membered cyclic hemiacetal while a furanose is a five-membered cyclic hemiacetal.

Epimers are sugars with a common structure, such as the arrangement of H and OH around carbon atoms, except for the carbon present at position or carbon number 2. Glucose and mannose, for example, are epimers of each other.

Anomers are the diastereomers that result during cyclization. Only the arrangement surrounding the first carbon C1, referred known as the anomeric carbon, differs (hemiacetal carbon atom).

02

Identifying α‐and β‐  anomers of pyranoses and furanoses

For anomer, hydroxy group (-OH) on the anomeric carbon is down (axial position) while for anomer, hydroxy group (-OH) on the anomeric carbon is up (equatorial position). Again, for anomer, the anomeric hydroxy(-OH) group is placed trans to the terminal -CH2OHgroup while for anomer, the anomeric hydroxy (-OH) group is placed cis to the terminalCH2OH group.

03

Structure of monosaccharides

(a) In chair conformation of Dmannopyranose, the anomeric carbon is C1 . The hydroxy group (-OH) on the anomeric carbon is down (axial position).

Dmannopyranose

In chair conformation of Dgalactopyranose, the anomeric carbon is C1. The hydroxy group (-OH) on the anomeric carbon is up (equatorial position).

Dgalactopyranose

(c) In chair conformation of Dalllopyranose, the anomeric carbon is C1 . The hydroxy group (-OH) on the anomeric carbon is up (equatorial position).


Dallopyranase

(d) In Haworth projection of Darabinofuranose, the anomeric carbon is C1. The hydroxy group (-OH) on the anomeric carbon is down which is trans to the terminal CH2OHgroup

Darabinofuranose

(e) In Haworth projection of , the anomeric carbon is . The hydroxy group on the anomeric carbon is up which is cis to the terminal CH2OHgroup.


Dribofuranose

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Most popular questions from this chapter

Cytosine, uracil and guanine have tautomeric forms with aromatic hydroxyl groups. Draw these tautomeric forms.

Question. (a) Figure 23-2 shows that the degradation of D-glucose gives D-arabinose, an aldopentose. Arabinose is most stable in its furanose form. Draw D-arabinofuranose.

(b) Ribose, the C2 epimer of arabinose, is most stable in its furanose form. Draw D-ribofuranose.

Question:

a) Draw D-allose, the C3 epimer of glucose.

b) Draw D-talose, the C2 epimer of D-galactose.

c) Draw D-idose, the C3 epimer of D-talose. Now compare your answers with Figure 23-3.

d) Draw the C4 鈥渆pimer鈥 of D-xylose. Notice that this 鈥渆pimer鈥 is actually an L-series sugar, and we have seen its enantiomer. Give the correct name for this L-series sugar.

Erwin Chargaff鈥檚 discovery that DNA contains equimolar amounts of guanine and cytosine and also equimolar amounts of adenine and thymine has come to be known as Chargaff鈥檚 rule:

G = C and A = T

(a) Does Chargaff鈥檚 rule imply that equal amounts of guanine and adenine are present in DNA? That is, does G = A?

(b) Does Chargaff鈥檚 rule imply that the sum of the purine residues equals the sum of the pyrimidine residues? That is, does A + G = C + T?

(c) Does Chargaff鈥檚 rule apply only to double-stranded DNA, or would it also apply to each individual strand if the double helical strand were separated into its two complementary strands?

Draw the Haworth projection for the cyclic structure of D-mannose by laying down the Fischer projection.

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