Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 3.8, Problem BQ
Interpretation Introduction

Interpretation:

The direction of rotation of plane polarised light must the common 19 chiral amino acids has to be given.

Concept Introduction:

Priority rules:

  • Priorities based on atomic number

-H,-CH3,-NH2,-OH,-SH,-Cl,-Br,-IIncreasingpriority

  • When priority cannot be assigned on the basis of the atoms bonded directly to the chiral center

-CH2H,-CH2CH3,-CH2NH2,-CH2OH,-CH2ClIncreasingpriority

  • Atoms participating in a double or triple bond are considered to be bonded to an equivalent number of phantom atoms.

For example,

Organic Chemistry, Chapter 3.8, Problem BQ

  • Priority assignment is made at the first point of difference between groups (should not be based on the larger group).

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Net charge and isoelectric point of an amino acid with an ionizable side group.Consider the net charge and isoelectric point of an amino acid with ionizable side (R-) group.(a) Identify the acidic amino acid(s) capable of having a negatively charged carboxyl side group.(b) Identify the basic amino acid(s) capable of having a positively charged amino side group.(c) For an amino acid with a side (R-) chain that can ionize to a negative charge, derive a general expression in terms of measured pH and known pKa values of α-carboxyla-amino (pKca), α-amino(pKaa),and side group (pKRa), respectively, for the net charge of  an amino acid Consider the net charge and isoelectric point of an amino acid with ionizable side (R-) group.(d) For an amino acid with a side (R-) chain that can ionize to a positive charge, derive a general expression in terms of measured pH and known pKa values ofα-carboxyl (pKca), α-amino (pKaa), and side group (pKRa), respectively, for the net charge of the amino acid.(e)…

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