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Chapter 23: Q23P (page 1226)

Show the products that result from hydrolysis of amygdalin in dilute acid. Can you suggest why amygdalin might be toxic to tumor (and possibly other) cells?

Short Answer

Expert verified

is released from amygdalin. It is potent and cytotoxic and neurotoxic in nature.

Step by step solution

01

Step-1. Hydrolysis of amygdalin in dilute acid:

Amygdalin is a naturally occurring chemical compound and is a cyanogenic glycoside as toxic cyanide ion can get released from it on its hydrolysis. Amygdalin on hydrolysis with dilute acid gives two molecules of glucose and benzaldehyde cyanohydrin as the products and further benzaldehyde cyanohydrin on hydrolysis gives hydrogen cyanide as the product.

Amygdalin Hydrogen cyanide

02

Step-2. Cyanide poisoning from amygdalin:

Amygdalin can cause cyanide poisoning as after its ingestion it is hydrolysed to give a molecule of hydrogen cyanide and two molecules of glucose. Enzymatic degradation of amygdalin occurs in three stages. Hydrogen cyanide is toxic to neurological system as well as it is cytotoxic meaning, cell killing. Due to cyanide poisoning, liver may get damaged and blood pressure could get drop very low.

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Most popular questions from this chapter

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

Trehalose is a nonreducing disaccharide (C12H22O11) isolated from the poisonous mushroom Amanita muscaria. Treatment with an 伪 -glucosidase converts trehalose to two molecules of glucose, but no reaction occurs when trehalose is treated with a 尾 -glucosidase. When trehalose is methylated by dimethyl sulfate in mild base and then hydrolyzed, the only product is 2,3,4,6-tetra-O-methylglucose. Propose a complete structure and systematic name for trehalose.

Raffinose is a trisaccharide (C18H32O16) isolated from cottonseed meal. Raffinose does not reduce Tollens reagent, and it does not mutarotate. Complete hydrolysis of raffinose gives D-glucose, D-fructose, and D-galactose. When raffinose is treated with invertase, the products are D-fructose and a reducing disaccharide called melibiose. Raffinose is unaffected by treatment with a-galactosidase, but an 伪 -galactosidase hydrolyzes it to D-galactose and sucrose. When raffinose is treated with dimethyl sulfate and base followed by hydrolysis, the products are 2,3,4-tri-O-methylglucose, 1,3,4,6-tetra-O-methylfructose, and 2,3,4,6-tetra-O-methylgalactose. Determine the complete structures of raffinose and melibiose and give a systematic name for melibiose.

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

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.
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