Concept explainers
a)
Interpretation:
The structure of threonine is to be elucidated using normal wedged and dashed line and the presence of two α-carbons in this amino acid gives it two chirality centers.
Concept introduction:
(2S,3R)-2-amino-3-hydroxybutanoic acid or threonine is an amino acid with two α-carbons and hence it has two chiral centers. According to the Fisher projections, the amino acid molecules may be represented using normal, wedged, and dashed lines.
To determine:
The structure of L-threonine using normal, wedged and dashed lines.
b)
Interpretation:
The structure of threonine is to be elucidated using normal wedged and dashed line and the presence of two α-carbons in this amino acid gives it two chirality centers.
Concept introduction:
(2S,3R)-2-amino-3-hydroxybutanoic acid or threonine is an amino acid with two α-carbons and hence it has two chiral centers. According to the Fisher projections, the amino acid molecules may be represented using normal, wedged, and dashed lines.
To determine:
Two possible diastereomers of L-threonine.
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Chapter 26 Solutions
Organic Chemistry
- h) Specify the absolute (R/S) configuration of the amino group in structure IV. (i) If the substituents in structures I, IV and V were identical (all OH or all NH2), which structure would result in a meso compound? (j) If each hydroxy group for structures I, II and VI were replaced with another amino group, which compound would be made optically inactive?arrow_forward(c) Label the following pair of molecules as homomer, enantiomer or diastereomer 2+1 ÇO,H ÇO,H Me () н. LOME Cl- "Ph and Cl and Ме H- -OMe H Ph Ét Etarrow_forwardDraw the Fisher projection formulas and perspective formulas of the stereoisomers of 3-amino-2-butanol. Assign R,S configuration to all chiral centers. Determine which among the isomers are enantiomers, diastereomers, and meso compounds.arrow_forward
- 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)…arrow_forwardDraw a 3-D structure of a molecule with a molecular formula of C4H9Cl containing one chiral center and draw its mirror image.arrow_forward(iv) Re-draw the amino acid below in a Fischer projection. H2N но, Mearrow_forward
- Draw a chiral molecule with two chiral centers and determine the absolute configuration (R or S) at each chiral center.arrow_forwardQ1: Are the following objects/molecules chiral? | H₂N H₂N Your foot I Glycine CO₂H CH3 Alanine CO₂H Chiralachiral Chiral / achiral Chiral / achiralarrow_forward(a) Identify type of molecules either chiral, achiral, or meso for each compound shown below and (b) Indicate the number of chiral centers in each molecule.arrow_forward
- Chemistry: Principles and PracticeChemistryISBN:9780534420123Author:Daniel L. Reger, Scott R. Goode, David W. Ball, Edward MercerPublisher:Cengage Learning