Peptides linkages

A purple or rose pink coloration i produced when sodium hydroxide and dilute copper sulphate solution are added to compounds containing two -CONH- groups attached either to one another, or to the same nitrogen atom, or to the same carbon atom. It is therefore also given by oxamide, NHjCO CONH, malonamide, NHtCO-CH, CONH, and by proteins and peptides. In fact the -COKH - is often spoken of as the peptide linkage. 

This reaction forms the basis of one method of terminal residue analysis A peptide is treated with excess hydrazine in order to cleave all the peptide linkages One of the terminal amino acids is cleaved as the free amino acid and identified all the other ammo acid residues are converted to acyl hydrazides Which amino acid is identified by hydrazmolysis the N terminus or the C terminus ... 

Proteias, amino acids bonded through peptide linkages to form macromolecular biopolymers, used as chiral stationary phases for hplc iaclude bovine and human semm albumin, a -acid glycoproteia, ovomucoid, avidin, and ceUobiohydrolase. The bovine semm albumin column is marketed under the name Resolvosil and can be obtained from Phenomenex. The human semm albumin column can be obtained from Alltech Associates, Advanced Separation Technologies, Inc., and J. T. Baker. The a -acid glycoproteia and ceUobiohydrolase can be obtained from Advanced Separation Technologies, Inc. or J. T. Baker, Inc. 

The peptide linkage is usually portrayed by a single bond between the carbonyl carbon and the amide nitrogen (Figure 5.3a). Therefore, in principle, rotation may occur about any covalent bond in the polypeptide backbone because all three kinds of bonds (N——C, and the —N peptide bond) are sin-... 

FIGURE 5.2 The peptide bond is shown in its usnal trans conformation of carbonyl O and amide H. The atoms are the oi-carbons of two adjacent amino acids joined in peptide linkage. The dimensions and angles are the average valnes observed by crystallographic analysis of amino acids and small peptides. The peptide bond is the light gray bond between C and N. (Adapted from Ramachandran, G. A., ct ai, 1974. Biochimica Biophysica Acta 359 298-302.)... 

In alkaline solution biuret, HN(CONH2)2 reacts with copper(II) sulfate to give a characteristic violet colour due to the formation of the complexes [Cu2(/l-OH)2(NHCONHCONH)4] (Fig. 28.6a) and [Cu(NHCONHCONH)2] . This is the basis of the biuret test in which an excess of NaOH solution is added to the unknown material together with a little CUSO4 soln a violet colour indicates the presence of a protein or other compound containing a peptide linkage. 

The hydantoin moiety has been utilized as a biostere for the peptide linkage, transforming a peptide lead into an orally available drug candidate. Therefore, an Arg-Gly-Asp-Ser tetrapeptide (18) lead structure was modified to a non-peptide RGD mimetic as an orally active fibrinogen receptor antagonist 19. ° ... 

Vancomycin, ristocetin A and teicoplanin are produced as fermentation products of Streptomyces orientalis, Nocardia lurida and Actinoplanes teichomyceticus, respectively. All three of these related compounds consist of an aglycone basket made up of fused macrocyclic rings and pendant carbohydrate moieties (Fig. 2-1). The macrocycles contain both ether and peptide linkages. The aglycones of vancomycin and teicoplanin contain two chloro-substituted aromatic rings, while the analogous portion of ristocetin A contains no chloro substituents. 

Tasks (1) and (2) are relatively easy to accomplish. The sample is first heated with hydrochloric acid to break all of the peptide linkages (amide bonds) in the protein. The resulting solution is then passed through a chromatographic column (recall the discussion on pp. 5-6 in Chapter 1). This separates the different amino acids and allows you to determine their identities and concentrations. 

Pascal An SI unit of pressure the pressure exerted by the force of 1 newton on an area of 1 square meter, 104,635 Paschen series, 138 Pasteur, Louis, 601 Pauli exclusion principle, 141-143 Pauling, Linus, 185 Pentyl propionate, 596t Peptide linkage The—C—N—group... 

Amino acids, the building blocks of giant protein molecules have a carboxyl group and an amino group attached to the same carbon atom (Fig. 3-10). A protein is a linear polymer of amino acids combined by peptide linkages. Twenty different amino acids are common in proteins. 

Note Primary amines yield fluorescent chromatogram zones even before the application of reagent 3. Secondary amines do not yield fluorescent derivatives until they have been treated with reagent 3. Hence, the reagent sequence allows the stepwise detection of primary and secondary amines. Taurine is preferred as the essential component of reagent 3 over the multiplicity of other possibilities because it produces intense fluorescence it is also not very volatile and is readily available. Amides and substances with peptide linkages, eg. hippuric acid, are not detected, neither are secondary amines that are volatile at high temperatures. 

If the individual residues of a peptide are transformed into the corresponding peptoid monomers to make hybrid oligomers, there will be a perturbation in the distance between side chains at the boundary between oligomer types. That is, spacing of side chains at a peptoid-peptide linkage will be different from that between either two peptide or peptoid residues. 

In peptide chemistry, the term "pseudopeptide" is commonly used to denote a peptide in which some or all of the amino acids are linked together by bonds other than the conventional peptide Linkage (13). Such pseudopeptides have found applications as specific structural... 

Proteins form in a sequence of condensation reactions in which the amine end of one amino acid combines with the carboxyl end of another, eliminating a water molecule to create an amide linkage. The amide group that connects two amino acids is called a peptide linkage, and the resulting molecule is known as a peptide. When two amino acids are linked, the product is a dipeptide. A dipeptide formed from alanine and glycine is shown in Figure 13-33. 

The four amino acids are joined with peptide linkages in the order given. Put the backbone in place as a line stmcture. Remember, however, that carbon atoms are not shown in line sfructures and hydrogens are included only for atoms other than carbon. 

The secondary structure of a protein is determined by hydrogen bonding between CDO and N—H groups of the peptide linkages that make up the backbone of the protein. Hydrogen bonds can exist within the same protein... 

C13-0116. The nitrogen atom of a peptide linkage has trigonal planar geometry. What is the hybridization of the nitrogen atom in a peptide linkage Explain why nitrogen adopts this form of hybridization. 

The broad use of A -carbonyldiimidazole (CDI) for the synthesis of amide and peptide linkages became a routine method only in the early sixties. JV-Protected amino acids were treated at room temperature with an equimolar amount of CDI to give imidazolides. Anhydrous tetrahydrofuran, dimethoxyethane, dichloromethane, pyridine, dimethylfor-mamide, and diethyl phosphite were utilized as solvents. In the second step the esters of amino acids, their hydrochlorides, or sodium salts were added to yield the peptide after several minutes or hours of reaction time. 

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