Biochemistry
9th Edition
ISBN: 9781319114671
Author: Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Publisher: W. H. Freeman
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What is the biologically-preferred stereochemistry and ionization states for the pentagon-peptide CANDY at a pH of 7?
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- Stereochemistry in biological molecules is often denoted by the D- and L- convention, instead of the R- and S- configurations determined by the Cahn-Ingold-Prelog methodology. Naturally occurring α-amino acids are typically in the L-configuration. The Fischer projection of L-alanine is shown. L-alanine H₂N- H3C- HOOC Identify which structures are equivalent to the L-configuration. H COOH H CH3 NH₂ -COOH NH₂ CH3 -H CH3 COOH H -NH₂ H₂N- H CH3 COOH NH₂ H CH3 -COOHarrow_forwardDraw a schematic of the chemical structure of the Leu-Tyr-Met-Lys tetrapeptide, with the correct ionization at neutral pH (pH 7). Also, give an estimate the pl of this tetrapeptide (you are given that the pKa of any acidic R group is 4, the pKa of any basic R group is 11.5, and the pKa of the α-COOH is 2, and the a-NH3 is 9.5). Provide rationale!arrow_forwardWhat is the principal form of arginine at pH 8.0? Approximately what fraction is in this form?arrow_forward
- Bb.45.arrow_forwardPhosphate buffers are commonly used to mimic biological systems. Given that phosophoric acid is a triprotic acid with three pKas (2.12, 7.21, and 12.32), why do you think this is? What are the dominant buffering compounds present in a phosphate buffer near physiological pH?arrow_forwardCalculate the pI of the peptide KLMRDSP (pKa = 3.5, 3.9, 9.5, 10.0, 12.5).arrow_forward
- The amino acid glycine is often used as an ingredient in buffers for biochemistry experiments. The amino group of glycine has a pKa of 9.6. Glycine exists in either a protonated form (-NH3+) or a free base (-NH₂). a) In what pH range can glycine be used as an effective buffer? b) In a 0.1M solution of glycine at pH 9.0, what fraction has its amino group in the protonated form? c) When 99% of the glycine is in the protonated from, what is the numerical relation between the pH of the solution and the pKa of the amino group?arrow_forwardHypoglycin A, an amino acid derivative found in unripened lychee, is an acutely toxic compound that produces seizures, coma, and sometimes death in undernourished children when ingested on an empty stomach. (a) Draw the neutral, positively charged, and negatively charged forms of hypoglycin A. (b) Which form predominates at pH = 1, 6, and 11? (c) What is the structure of hypoclycin A at its isoelectric point?arrow_forwardWhat is the molecular basis for the observation that the overall charge on a protein becomes increasingly positive as pH drops and more negative as pH increases?arrow_forward
- At which pH would the peptide with the amino acid sequence 'KEYHR' be found in an IPG (Immobilized pH gradient) strip after successful isoelectric focusing. Show calculation. lonizable groups Alpha amine group of K Side chain group of K Side chain group of E Side chain group of Y Side chain group of H Side chain group of R Alpha carboxylic acid group of R pka 8.95 10.53 4.25 10.07 6 12.48 2.17arrow_forwardWhat is the net charge on the peptide RHTLE at pH 12.5?arrow_forwardWhat is the charge on the following peptide at standard biochemical pH? S-Y-D-F-K-I-V-F-L-L +2 -1 0 0 0-2 O +1arrow_forward
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