Carbodiimides are excellent coupling agents to use to allow an amide or ester coupling to occur under milderconditions. DCC (dicyclohexylcarbodiimide) is extremely common, but the byproduct is insoluble and cancontaminate products, whereas other coupling agents have different byproducts with different products. DIC(diisopropylcarbodiimide) and its byproduct are soluble and are easily removed from a solid-phase synthesis.Draw a full mechanism for the amide coupling shown below using DIC as a coupling agent.OHCH3NH₂-N=C=N-baseHINT: The first step of the mechanism uses the organic base to deprotonate something...lohexane asWhen doing solid-phase peptide synthesis, it is vitally important to get the amino acids in the correct order.However, all amino acids have an amine handle and a carboxylic acid handle, so it's easy to couple an aminoacid with itself or in the wrong sequence.How can a chemist ensure that they make only the sequence Gly-Ala-Arg, without ending up with the aminoacids coupling in the wrong order or duplicated in the sequence?

The reagent DIC also called carbodiimide is a coupling agent for ester or amide formation. The…

Carbodiimides are excellent coupling agents to use to allow an amide or ester coupling to occur under milder conditions. DCC (dicyclohexylcarbodiimide) is extremely common, but the byproduct is insoluble and can contaminate products, whereas other coupling agents have different byproducts with different products. DIC (diisopropylcarbodiimide) and its byproduct are soluble and are easily removed from a solid-phase synthesis. Draw a full mechanism for the amide coupling shown below using DIC as a coupling agent. OH CH3NH2 -N=C=N- base HINT: The first step of the mechanism uses the organic base to deprotonate something...

Carbodiimides are excellent coupling agents to use to allow an amide or ester coupling to occur under milder conditions. DCC (dicyclohexylcarbodiimide) is extremely common, but the byproduct is insoluble and can contaminate products, whereas other coupling agents have different byproducts with different products. DIC (diisopropylcarbodiimide) and its byproduct are soluble and are easily removed from a solid-phase synthesis. Draw a full mechanism for the amide coupling shown below using DIC as a coupling agent. OH CH3NH2 -N=C=N- base HINT: The first step of the mechanism uses the organic base to deprotonate something...

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Carbodiimides are excellent coupling agents to use to allow an amide or ester coupling to occur under milder
conditions. DCC (dicyclohexylcarbodiimide) is extremely common, but the byproduct is insoluble and can
contaminate products, whereas other coupling agents have different byproducts with different products. DIC
(diisopropylcarbodiimide) and its byproduct are soluble and are easily removed from a solid-phase synthesis.
Draw a full mechanism for the amide coupling shown below using DIC as a coupling agent.
OH
CH3NH₂
-N=C=N-
base
HINT: The first step of the mechanism uses the organic base to deprotonate something...
lohexane as
When doing solid-phase peptide synthesis, it is vitally important to get the amino acids in the correct order.
However, all amino acids have an amine handle and a carboxylic acid handle, so it's easy to couple an amino
acid with itself or in the wrong sequence.
How can a chemist ensure that they make only the sequence Gly-Ala-Arg, without ending up with the amino
acids coupling in the wrong order or duplicated in the sequence?

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