The Arg-Gly-Asp tripeptide (RGD) is a well-known tumour targeting peptide motif. Explain how you would synthesise H-Arg-Gly-Asp-OH, starting from the constituent amino acids? Explain all steps that are necessary and discuss a mechanism for one side chain protection and one C terminus protection.

The Arg-Gly-Asp tripeptide (RGD) is a well-known tumour targeting peptide motif. Explain how you would synthesise H-Arg-Gly-Asp-OH, starting from the constituent amino acids? Explain all steps that are necessary and discuss a mechanism for one side chain protection and one C terminus protection.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter26: Biomolecules: Amino Acids, Peptides, And Proteins

Section26.6: Peptide Sequencing: The Edman Degradation

Problem 15P: Give the amino acid sequence of hexapeptides that produce the following sets of fragments upon...

See similar textbooks

Related questions

Q: Show the peptides that would result from cleavage by the indicated reagent:…

A: Trypsin is another type of protease or peptidase that cleaves at the C-terminal of lysine or…

Q: indicate which of the amino acid residues in the following peptide sequence contains a group that…

A: When the carboxyl group of one molecule reacts with the amino group of the other molecule, releasing…

Q: The cleavage pattern for o-lodosobenzoate is C-terminal to tryptophan; the cleavage pattern for…

Q: identify the presence of a peptide bonds in your structure by putting a star/highlighting at the…

A: The compound given is,

Q: Show the peptides that would result from cleavage by the indicated reagent:…

A: To determine the peptides that result from cleavage by the indicated product as shown below, The…

Q: A decapeptide undergoes partial hydrolysis to give peptides whose amino acid compositions are shown.…

A: There are some selective reagents which are mainly utilized to recognize the sequence of particular…

Q: After treatment with peroxyformic acid, the peptide hormone vasopressin is partiallyhydrolyzed. The…

A: The fragments are given as follows:

Q: Estimate the charge of the following oligopeptides at pH 7 based on the pKa values of the…

Q: Treatment of a new protein with dansyl chloride reveals two (2) dansyl-labelled derivatives of amino…

Q: Explain why the pKa of the - NH3+ group of an a-amino acid is lower than the pKa of the ammonium ion…

A: In primary (1o) amine, RNH3+, the -NH3+ group is attached to the electron-donating group that is…

Q: Which of the following clarifications is false? Select one: to. fibroin contains AA with sparse side…

A: Fibroin is a type of protein present in silk. Structurally, it has large widely spread amino acids…

Q: Bradykinin is a linear nonapeptide released by blood plasma globulin in response to a wasp sting.…

A: The peptide contains 9 amino acids.

Q: Explain why the ability of PLP to catalyze an amino acid transformation is greatly reduced if a…

A: The basic step is when PLP catalyzes amino acid's trasformation by the removal of the proton from…

Q: Based on the given figure, a. what is the possible identity of the amino acid? b. what is the…

A: Since you have asked a question with multiple subparts, we will answer only first 3 subparts for…

Q: A nonapeptide released by globulins in the blood in response to a wasp sting. Hydrolysis gives the…

A: Given: We have to prepare nanopeptide.

Q: Another strategy used to resolve amino acids involves converting the carboxy group to an ester and…

A: In alanine one stereogenic center is present. The carboxylic group of both enantiomers of alanine…

Q: With reference to the following peptide: (a) Identify the N-terminal and Cterminal amino acids. (b)…

A: In given model the black ball represent carbon atoms, white represent hydrogen atoms, blue…

Q: At pH 9.0, which of the peptides listed in Question #4 would be predicted to not bind to an anion…

A: In an anion exchange column, anions (i.e.), negatively charged species are retained in the column.…

Q: Determine the amino acid sequence of a polypeptide from the following data: Acid-catalyzed…

A: Given polypeptide chain has 13 amino acids in its sequence. In the given polypeptide, N-terminal…

Q: 1A) Draw a peptide solely derived from L- amino acids. 1B) Note all stereocenters and assign R,S…

A: Isomers are the species that have the same molecular formula but due to differences in the molecular…

Q: Oxytocin, a nonapeptide hormone secreted by the pituitary gland, functions by stimulating uterine…

A: primary sequence of oxytocin

Q: Specify the absolute (R/S) configuration of the amino group in structure IV. (i) If the…

Q: a) With the help of a schematic diagram describe the synthesis of the tripeptide Phe-Leu- Met using…

Q: Write out the steps needed to synthesize the following peptide using the Merrifield method.

A: Merrifield Method: In this method, the peptide is being produced by the removal of water from the C…

Q: In a variation of the Merrifield solid-phase peptide synthesis, the amino group is protected by a…

A: In organic chemistry, protecting groups are used to protect a molecule so that it can’t participate…

Q: Cyclic peptides received increasing amounts of attention because of their pharmaceutical propertie…

A: Cyclic peptides have much importance in Pharmaceutical industries. This cyclic peptides are formed…

Q: H2N- CH-C- NH- CH2-C-NH-CH2- NH-CH-C-NH-CH-C-OH CH2 CH2 CH2 CH Compound A (Leu-enkephalin) H3C CH3…

A: Since you have asked multiple questions we will answer the first one for you. To get the remaining…

Q: Suggest a scheme you will follow to synthesise the dipeptide Ala-Gly

Q: The peptide Proline-Serine-Alanine-Phenylalanine-Glutamine is present at pH 7. Draw the peptide and…

Q: Which of the following peptides have a net positive chargeat pH 7? (a) Gly-Ser-Lys, (b) Pro-Leu-Ile,…

A: Among the 20 common amino acids, five have a side chain which can be charged. At pH=7, two are…

Q: Calculate the pI of this peptide. Calculate the net charge of this peptide at pH 2, pH 7, and pH 11.

Q: Draw a structure for a peptide that gives Gly, Ile & Phe on hydrolysis and fails to react with…

A: Amino acids are the building blocks of proteins. Peptides are formed by the combination of two or…

Q: Explain how you would synthesise the dipeptide, H-Glu-Phe-OH, starting from the constituent amino…

Q: Write out a stepwise sequence that shows how a racemic mixture of leucine enantiomers can be…

A: The given recemic mixture of leucine enantiomers. The (S)-form and (R)-forms react with the given…

Q: Taking the structure of the amino acids into account, give a comparative discussion pK values where…

Q: Alanine is a diprotic amino acid with a pk, = 2.344 for the carboxylic group and a pka = 9.868 for…

A: Ajj

Q: The bottom peptide segment is found in the secondary structure composed of anti-parallel - sheets.…

Q: 13. Explain why the dansyl chloride treatment of a single polypeptide chain followed by its complete…

A: Dansyl chloride is a reagent which reacts with primary amino groups present in aromatic amines as…

Q: 20. After treatment with peroxyformic acid, the peptide hormone vasopressin is partially hydrolyzed.…

A: In the peptide chain , amino group is at the left . By looking at the fragments pattern we get the…

Q: Draw the molecule arginyl-alanyl-histidyl-cysteinyl-isoleucyl-asparagine at pH 7. List the name of…

A: As per the policy, we are only allowed to answer only first question. For the answers of other…

Q: Show the peptides that would result from cleavage by the indicated reagent:…

A: Carboxypeptidase A is a type of exopeptidase.This indicates that it is responsible for hydrolysis of…

Q: Suggest a reasonable strategy for the synthesis of the dipeptide Leu-Phe, using established protocol…

A: The biomolecules which have carboxylic and amine group containing monomer units are known as…

Q: Draw a dipeptide with alanine (R = CH3) at the C-terminus and serine (R = CH2OH) at the N- terminus.…

Question

The Arg-Gly-Asp tripeptide (RGD) is a well-known tumour targeting peptide
motif. Explain how you would synthesise H-Arg-Gly-Asp-OH, starting from
the constituent amino acids? Explain all steps that are necessary and discuss a
mechanism for one side chain protection and one C terminus protection.

Expert Solution

This question has been solved!

Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.

SEE SOLUTION Check out a sample Q&A here

Step 1

Step 2

Step 3

Step 4

Step by step

Solved in 4 steps with 4 images

SEE SOLUTION Check out a sample Q&A here

Knowledge Booster

Metals in Transport, Tranfer and Transcription

Learn more about

Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.

Similar questions

Draw the structure of the tetrapeptide Asp-Arg-Val-Tyr. Please show the appropriate stereochemistry of the natural amino acids in the resulting peptide. Please draw all ionizable groups in their neutral form.
Imagine the main chain of a protein bends back on itself, so that two amino acid residues R₁ and R₂ come close to each other. Here's what R₁ loo -CH- CH₂ CH₂ CH₂ NH H₂N NH₂ Could R₁ form a salt bridge with R, at physiological pH, if R₂ were the right kind of residue? O yes O no If you said R₁ could form a salt bridge with R₂, what would R₂ have to be? 0 If there's only one possibility, write its 3-letter code. If there is more than one possibility, write the 3-letter code of any of them. X
Draw three-dimensional representations of the following amino acids.(a) l-phenylalanine (b) l-histidine (c) d-serine (d) l-tryptophanDraw three-dimensional representations of the following amino acids.(a) l-phenylalanine (b) l-histidine (c) d-serine (d) l-tryptophan
Draw the structure of the peptide ENDQCW. Draw the stereochemistry of the amino acids. Show the ionization state that would be the major form at pH 1. What is the isoelectric point of the peptide?
Treatment of a new protein with dansyl chloride reveals two (2) dansyl-labelled derivatives of amino acids, alanine and methionine. What can you deduce about the structure of the proteinfrom these results?
2 Consider the following peptides: (a) Lys-Leu-Met-Phe-Gln (b) lle-Gly-Thr-Asn-Val (c) Arg-Phe-Leu-His-Lys (d) Tyr-Glu-Gln-Asp-Pro (e) Cys-Val-Asp-Asn-Leu Which one of the peptides would have the greatest solubility at pH 1? (a) (b) (c) (d) (e) Consider the following peptides: (a) Lys-Leu-Met-Phe-Gln (b) lle-Gly-Thr-Asn-Val (c) Arg-Phe-Leu-His-Lys (d) Tyr-Glu-Gln-Asp-Pro (e) Cys-Val-Asp-Asn-Leu Which one of the peptides would have the greatest solubility at pH 14? (a) (b) (c) (d) (e)
Outline the steps needed to synthesize the tetrapeptide Ala–Leu–Ile–Gly using the Merrifield technique.
In a paragraph form provide the experimental procedure of the reaction of oxazetidine-containing peptides and α-ketoacid that will result in protein that contain native serine residues
1 Based on the structural properties of 7EHE, how resistant (or sensitive) would your protein be to heat denaturation and why?
As a genetic engineer, you have been given the following task:alter a protein’s structure by converting a specific amino acidsequence that forms an extended a-helix to one that formsa b-barrel. What types of amino acid are probably in thea-helix, and which ones would you need to substitute?
Which of the following peptides have a net positive charge at pH 7? (a) Gly-Ser-Lys
(a) An aliphatic aminoglycoside is relatively stable to base, but it is quickly hydrolyzed bydilute acid. Propose a mechanism for the acid-catalyzed hydrolysis.NHHCH2RR2NH2 + sugarRHHOH OHOH Oan aliphatic ribosideH3O+ +(b) Ribonucleosides are not so easily hydrolyzed, requiring relatively strong acid.Using your mechanism for part (a), show why cytidine and adenosine (for example)are not so readily hydrolyzed. Explain why this stability is important for livingorganisms.