Answered step by step
Verified Expert Solution
Link Copied!

Question

1 Approved Answer

The fluorenylmethoxycarbonyl group is used to protect the amino group of amino acids during the Merrifield solid phase peptide synthesis procedure. The group is then

image text in transcribed
The fluorenylmethoxycarbonyl group is used to protect the amino group of amino acids during the Merrifield solid phase peptide synthesis procedure. The group is then removed by treatment with piperidine. The mechanism of addition and removal is as follows: 1. The amino acid under basic conditions reacts with Fmoc chloride followed by deprotonation to give tetrahedral intermediate 1; 2. collapse of the tetrahedral intermediate gives the Fmoc-aa; 3. in the removal sequence, deprotonation of the tertiary carbon gives carbanion 1; 4. elimination gives 9-methylene fluorene and carbamate 2; 5. decarboxylation gives CO2 and the amino acid. CI FMOC chloride Work out the above mechanism on a separate sheet of paper and then draw the structure of Fmoc-aa. You do not have to consider stereochemistry, Use Ri to represent a generic R group for the amino acid. The R group tool is located in the charges and lone pairs drop-down menu. P opy to [F

Step by Step Solution

There are 3 Steps involved in it

Step: 1

blur-text-image

Get Instant Access to Expert-Tailored Solutions

See step-by-step solutions with expert insights and AI powered tools for academic success

Step: 2

blur-text-image

Step: 3

blur-text-image

Ace Your Homework with AI

Get the answers you need in no time with our AI-driven, step-by-step assistance

Get Started

Recommended Textbook for

Risk Management And Financial Institution

Authors: John C. Hull

2nd Edition

0136102956, 9780136102953

More Books

Students also viewed these Finance questions