Hydroxyproline solubility

HydTOX5 proline-derived polyesters are usually readily soluble in a variety of organic solvents (benzene, toluene, chloroform, dichloro-methane, carbon tetrachloride, tetrahydrofuran, dimethylformamide, etc.) As expected, the solubility in hydrophobic solvents increased with increasing chain length of the N protecting group, while the solubility in polar solvents decreased. For example, poly(N-hexanoyl-hydroxyproline ester) is slightly soluble in ether but easily soluble in acetonitrile, while poly(N-palmitoylhydroxyproline ester) is readily soluble in ether but virtually insoluble in acetonitrile. 

The method of protein hydrolysis was important acid hydrolysis caused destruction of tryptophan but alkaline treatment gave even greater losses of other amino acids especially cystine. The amino acids were usually separated by then standard chemical procedures based on differences in solubility, selective precipitation by agents such as Reinecke salt (proline and hydroxyproline), or flavianic acid (arginine). 

This chapter deals with the very important a-amino acids, the building blocks of the proteins that are necessary for the function and structure of living ceils. Enzymes, the highly specific biochemical catalysts are proteins. or-Amino acids are dipolar ions (zwitterions), RCH(N" H,)COO , as is indicated by their crystallinity, high melting point, and solubility in water rather than in nonpolar solvents. The standard (naturally occurring) amino acids are listed in Table 21-1 those marked with an asterisk are essential amino acids that cannot be synthesized in the body and so must be in the diet. They have 1° NHj s except for proline and hydroxyproline (2°). They have different R groups. 

Ascorbic Acid Is Required to Maintain the Enzyme that Forms Hydroxyproline Residues in Collagen Vitamin B12 Coenzymes Are Associated with Rearrangements on Adjacent Carbon Atoms Iron-Containing Coenzymes Are Frequently Involved in Redox Reactions Metal Cofactors Lipid-Soluble Vitamins... 

To improve the aqueous solubility of 5 we also synthesized a cyclopeptide 6 containing hydroxyproline subunits [24]. Although this compound is very water-soluble, and in solution adopts a similar conformation to 5, it only forms 1 1 complexes with anions. A reason for the inability of 7 to form 2 1 complexes could be that the hydroxyproline subunits in 6 are better solvated than prolines in aqueous solution, and the desolvation required for aggregation of two cyclopeptide molecules thus occurs less readily. Steric hindrance of hydroxyl groups from different cydopeptide moieties in the a dimeric complex of 6 could, moreover, also make aggregation difficult. Although peptide 6 cannot form sandwich-type complexes, it proved to be valuable for a quantitative determination of the anion affinity of 5, the results of which are summarized in Table 2.2.3 [24],... 

According to this proposal, the incorporation of proline into collagen follows the acyl adenylate and acyl RNA stages now generally believed to occur in protein synthesis. A bound hydroxyproline intermediate is postulated, from which hydroxyproline is transferred to soluble RNA. We prefer to suggest that different RNA acceptor molecules exist for hydroxyproline and proline this would be consistent with recent work which indicates that the soluble RNA molecule contains the information for incorporation of a particular amino acid into protein (3). Although it is conceivable that there is hydroxylation of prolyl-sRNA to yield hydroxyprolyl-sRNA, an additional mechanism would be needed... 

Properties Colorless crystals. Very soluble in water slightly soluble in alcohol insoluble in ether. Optically active, dZ-hydroxyprolinc, mp 261-262C with decomposition.Z-hydroxyproline, mp 270C (natural). rZ-hydroxyproline, mp 274C. 

Hurych and Chvapil have implicated free tissue hydroxyproline as a breakdown product of newly formed soluble collagens in labeled studies in animals. These implications have not been studied in man (H13). 

J4. Jasin, H. E., and Ziff, M., Relationship between soluble collagen and urinary hydroxyproline in the lathyritic rat. Proc. Soc. ExpU. Biol. Med. 110, 837-841 (1962). 

The answer is e. (Murray, pp 627-661. Sciiver, pp 3897-3964. Sack, pp 121-138. Wilson, pp 287-320.) Ascorbic acid (vitamin C) is found in fresh fruits and vegetables. Deficiency of ascorbic acid produces scurvy, the sailor s disease. Ascorbic acid is necessary for the hydroxylation of proline to hydroxyproline in collagen, a process required in the formation and maintenance of connective tissue. The failure of mesenchymal cells to form collagen causes the skeletal, dental, and connective tissue deterioration seen in scurvy. Thiamine, niacin, cobalamin, and pantothenic acid can all be obtained from fish or meat products. The nomenclature of vitamins began by classifying fat-soluble vitamins as A (followed by subsequent letters of the alphabet such as D, E, and K) and water-soluble vitamins as B. Components of the B vitamin fraction were then given subscripts, e.g., thiamine (Bi), riboflavin (B2), niacin [nicotinic acid (B3)], panthothenic acid (B5), pyridoxine (Bg), and cobalamin (B ). The water-soluble vitamins C, biotin, and folic acid do not follow the B nomenclature. 

However, soluble metal chiral complex catalysts are better, even though ketone hydrogenation under these conditions is more difficult to run than olefin hydrogenation. Notable achievements have been made using Rh and Ru metals. Phosphine ligands are often used, which contain either an asymmetric alkyl group have the phosphorous atom as the asymmetric center, or have an axial element of chirality (atropisomerism) . Other chiral ligands commonly used are derived from amino acids, from L-hydroxyproline and from ferrocene. 

Increase in TCA soluble nitrogen or hydroxyproline per mg of enzyme protein per minute at 40° C. 

The water-insoluble fraction was more readily digested than the water-soluble fraction. Heat denaturation naturally made meat proteins more readily digested by these enzymes, and the effect of denaturation was more significant in the water-soluble fraction than the other fraction. As expected, hydrolysis of the native connective tissue by these enzymes as indicated by increased hydroxyproline was extremely low. Connective tissue after heat denaturation was readily hydrolyzed. Papaya peptidase A showed about a fivefold increase while papain and chymopapain increased their hydrolyses seven- to tenfold. 

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