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 27, Problem 27.18P
Interpretation Introduction
Interpretation:
The Fischer projections and three dimensional representations for the amino acids D-valine, D-asparagine and D-glutamic acid has to be drawn.
Concept Introduction:
The two dimensional representation of the molecules is known as Fischer projection. In Fischer projection, the atoms present on the horizontal plane are facing towards the front and the atoms present on the vertical plane are away from the plane. In D-amino acids, when represented in Fischer projection the
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Although only l-amino acids occur in proteins, d-amino acids are often a part of the metabolism of lower organisms. The antibiotic actinomycin D, for example, contains a unit of d-valine, and the antibiotic bacitracin A contains units of d-asparagine and d-glutamic acid. Draw Fischer projections and three-dimensional representations for these three d-amino acids.
Assign an R or S configuration to the chiral center in each amino acid.
(a) l-Phenylalanine (b) l-Glutamic acid (c) l-Methionine
1.Draw Fischer projection formulas for the following amino acids.
L-Serine
D-Serine
D-Alanine
L-Leucine
2. Draw the structure of alanylglutamylglycyllysine
Chapter 27 Solutions
Organic Chemistry
Ch. 27.1 - Of the 20 protein-derived amino acids shown in...Ch. 27.2 - Prob. 27.2PCh. 27.2 - Prob. 27.3PCh. 27.3 - Draw a structural formula for Lys-Phe-Ala. Label...Ch. 27.4 - Which of these tripeptides are hydrolyzed by...Ch. 27.4 - Deduce the amino acid sequence of an undecapeptide...Ch. 27.6 - Prob. 27.7PCh. 27 - What amino acid does each abbreviation stand for?...Ch. 27 - The configuration of the chiral center in -amino...Ch. 27 - Assign an R or S configuration to the chiral...
Ch. 27 - Prob. 27.11PCh. 27 - Prob. 27.12PCh. 27 - Draw zwitterion forms of these amino acids. (a)...Ch. 27 - Prob. 27.14PCh. 27 - Why is Arg often referred to as a basic amino...Ch. 27 - Prob. 27.16PCh. 27 - Prob. 27.17PCh. 27 - Prob. 27.18PCh. 27 - Prob. 27.19PCh. 27 - Prob. 27.20PCh. 27 - Both norepinephrine and epinephrine are...Ch. 27 - Prob. 27.22PCh. 27 - Draw a structural formula for the form of each...Ch. 27 - Prob. 27.24PCh. 27 - Write the zwitterion form of alanine and show its...Ch. 27 - Prob. 27.26PCh. 27 - Write the form of aspartic acid most prevalent at...Ch. 27 - Prob. 27.28PCh. 27 - Prob. 27.29PCh. 27 - For lysine and arginine, the isoelectric point,...Ch. 27 - Prob. 27.31PCh. 27 - Account for the fact that the isoelectric point of...Ch. 27 - Prob. 27.33PCh. 27 - Prob. 27.34PCh. 27 - At pH 7.4, the pH of blood plasma, do the majority...Ch. 27 - Prob. 27.36PCh. 27 - Prob. 27.37PCh. 27 - Prob. 27.38PCh. 27 - A chemically modified guanidino group is present...Ch. 27 - Draw a structural formula for the product formed...Ch. 27 - Prob. 27.41PCh. 27 - Prob. 27.42PCh. 27 - A decapeptide has the following amino acid...Ch. 27 - Following is the primary structure of glucagon, a...Ch. 27 - Prob. 27.45PCh. 27 - Draw a structural formula of these tripeptides....Ch. 27 - Estimate the pI of each tripeptide in Problem...Ch. 27 - Glutathione (G-SH), one of the most common...Ch. 27 - Following are a structural formula and a...Ch. 27 - Prob. 27.50PCh. 27 - Prob. 27.51PCh. 27 - Prob. 27.52PCh. 27 - Prob. 27.53PCh. 27 - Prob. 27.54PCh. 27 - Distinguish between intermolecular and...Ch. 27 - Prob. 27.56PCh. 27 - Prob. 27.57P
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- Except for cysteine, only S amino acids occur in proteins. Several R amino acids are also found in nature, however. (R)-Serine is found in earthworms, and (R)-alanine is found in insect larvae. Draw Fischer projections of (R)-serine and (R)-alanine. Are these d or l amino acids?arrow_forwardAnswer the following questions about the amino acid whose Fischer projection formula is a. Is it a D-amino acid or an L-amino acid? b. Is it a nonpolar or polar amino acid? c. Is it an essential or nonessential amino acid? d. Is it a standard or nonstandard amino acid?arrow_forwardIf the side chain of the amino add is a methyl group, the compound is referred to as alanine. What is the Cahn-Ingold-Prelog stereochemical descriptor for the chiral center in alanine? 1. It is a Z-stereocenter. 2. It is an S-stereocenter. 3. It is an E-stereocenter. 4. It is an R-stereocenter.arrow_forward
- The configuration of the chiral center in a-amino acids is most commonly specified using the d,l convention. It can also be identified using the R,S convention . Does the chiral center in l-serine have the R or S configuration?arrow_forwardExplain the formation of thioether-linked prenyl anchor proteinsarrow_forwardWHICH OF THESE STATEMENTS ARE TRUE AND WHICH ARE FALSE The D-amino acid is the enantiomer of the L-amino acid. The D-amino acid has a different melting point and boiling point than the L-amino acid. If the L-amino acid has an optical rotation of +34o, the D-amino acid is also +34o. A 50/50 mixture of the D- and L-amino acid is optically active. There is no conjugated component in either the D- or L-amino acid.arrow_forward
- Draw three-dimensional representations of the following amino acids.(a) l-phenylalaninearrow_forwardDraw three-dimensional representations of the following amino acids. ) d-serinearrow_forwardPart 1 Show the complete steps and products of the Haworth Projection structure of the following saccharides. The males have to answer the structure of D-fructose and the females are the structure of D-galactose. Expanded structure of the given molecule Fischer Projection Haworth's structure [show the complete steps] Step 1 Step 2 Step 3 Part 2 Show the synthesis of disaccharide lactose. Give the expanded structure of the reactants. Give the expanded structure of the products. Part 3. Show the chemical reaction of D-ribose. Name the chemical reaction. Show here the chemical equation and name the products. Use the expanded structure. 1. 2. 3.arrow_forward
- Where can you find the acyl group in the structure? A. At the 1-amino position of the sugar B. At the 1-amino position of the streptamine C. At the 1-amino position of the 2-deoxystreptamine At the 3-amino position of streptamine D. At the 3-amino position of 2-deoxystreptamine E. At the OH-position of the amino sugararrow_forward1. A. Draw the structure of L-valine in a strongly basic solution. B. What is the charge of this amino acid in a strongly basic solution?arrow_forwardDraw the stereoisomers of the following amino acids. Indicate pairs of enantiomers and pairs of diastereomers.arrow_forward
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Biomolecules - Protein - Amino acids; Author: Tutorials Point (India) Ltd.;https://www.youtube.com/watch?v=ySNVPDHJ0ek;License: Standard YouTube License, CC-BY