Apparently the economically important chain reaction, wool \(+\) moths \(\rightarrow\) holes \(+\) more moths, has, as a key step, scission of the disulfide linkages of cystine in the polypeptide chains by the digestive enzymes of the moth larva. Devise a method of mothproofing wool which would involve chemically altering the disulfide linkages

Short Answer

Expert verified
To mothproof wool by chemically altering the disulfide linkages of cystine in the polypeptide chains, the following method can be used: First, convert the disulfide bonds to thiol groups using a mild reducing agent like tris(2-carboxyethyl)phosphine (TCEP). Then, react the thiol groups with a suitable crosslinking agent, such as divinyl sulfone, to form a more stable linkage that is less susceptible to cleavage by moth enzymes. Apply this treatment to wool fabric, allowing the chemicals to penetrate and react with the disulfide linkages within the wool fibers, and then wash and dry the fabric. The treated fabric should be more resistant to moth digestion, preventing holes and moth infestations.

Step by step solution

01

Understanding the chemical structure of wool and the moth digestion process

Wool is mainly composed of a protein called keratin, which consists of a series of amino acids connected by peptide bonds. One of these amino acids is cystine, which contains a disulfide bond (S-S). Moth larvae produce enzymes that can break these disulfide bonds, allowing them to digest the wool.
02

Idea for modification of disulfide linkages

Since the key step for moth digestion involves breaking the disulfide bonds of cystine, we can make it more difficult for the larvae by chemically modifying these linkages. One such approach is to replace the disulfide bonds with linkages that are not prone to cleavage by the moth enzymes. For example, we could use a reducing agent to convert the disulfide bonds into thiol groups (SH), and then react these thiol groups with a suitable reagent to form a more stable bond.
03

Conversion of disulfide bonds to thiol groups

We can use a mild reducing agent like tris(2-carboxyethyl)phosphine (TCEP) to convert the disulfide bonds of cystine to thiol groups (SH). TCEP would break the disulfide bond in cystine, resulting in the formation of free thiol groups: R-S-S-R + 2 TCEP \(\rightarrow\) 2 R-SH + TCEP-oxide Here, R represents the rest of the amino acid.
04

Reaction of thiol groups with a suitable reagent

To stabilize the thiol groups and make them resistant to moth enzymes, we can react the free thiol groups with a suitable reagent to form a more stable linkage. One example is to react the thiol groups with a crosslinking agent such as divinyl sulfone: 2 R-SH + Divinyl sulfone \(\rightarrow\) R-S-CH2-CH2-S-R This forms a new linkage between the cystine amino acids, which is less susceptible to cleavage by moth enzymes.
05

Applying the treatment to wool fabric

The method described above can be applied to wool fabric by creating a treatment solution containing the reducing agent and the crosslinking agent. The wool fabric would be immersed in the treatment solution, allowing the chemicals to penetrate and react with the disulfide linkages within the wool fibers. Once the treatment is complete, the wool fabric can be washed to remove any unreacted chemicals, and subsequently dried. The resulting fabric should be more resistant to moth digestion, thus preventing holes and moth infestations.

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