The Relative Stability of Internal Metal Complexes. II. Metal Derivatives of 8-Hydroxyquinoline 5-Sulphonic Acid and a Series of Monocarboxylic Mono-α-amino Acids including Histidine

1949 ◽  
Vol 2 (4) ◽  
pp. 579 ◽  
Author(s):  
LE Maley ◽  
DP Mellor

Stability constants of ct series of metal complexes derived from the series of α-amino acids, glycine, alanine, leucine, valine, histidine, and 8-hydroxyquinoline 5-sulphonic acid have been determined by an electrometric method. The metals fall in the same order, as regards stability of their complexes, as was found for the chelating molecules studied in Part I of this series. As the length of the a chain of the amino acid increases, there is a small decrease in the stability of the amino acid complexes of any one metal. The cobalt II complex of histidine is much more stable than cobalt II complexes derived from any of the other α-amino acids. It is suggested that this explains why histidine is able to nullify the inhibiting action of cobalt on the growth and respiration of various aerobic and anaerobic organisms. Though there is no great difference in the stability of corresponding metal complexes derived from 8-hydroxyquinoline and 8-hydroxyquinoline 5-sulphonic acid (when allowance is made for different solvents used in making the measurements), there is a marked difference in the bacteriostatic action of these two chelating molecules. A reason for this difference is suggested. The stability constants of any chelating reaction involving the liberation of any number of hydrogen ions can be evaluated by using the generalized mathematical treatment which has been set out in this series of papers.

1996 ◽  
Vol 61 (2) ◽  
pp. 288-297 ◽  
Author(s):  
Vladimír Pouzar ◽  
Ivan Černý

New approach to the preparation of steroids with connecting bridge, based on an O-carboxymethyloxime (CMO) structure, and with terminal hydroxy group, is presented. 17-CMO derivatives of 3β-acetoxy- and 3β-methoxymethoxyandrost-5-en-17-one were condensed with α,ω-amino alcohols to give derivatives with a chain of seven to nine atoms. After THP-protection, these compounds were converted to 3-keto-4-ene derivatives. An alternative synthesis consisted in transformation of 17-CMO derivatives with bonded amino acids by reduction of the terminal carboxyl. The resulting compounds were designed as building blocks for the preparation of bis-haptens for sandwich immunoassays.


Synthesis ◽  
2019 ◽  
Vol 51 (05) ◽  
pp. 1273-1283 ◽  
Author(s):  
Simon Baldauf ◽  
Jeffrey Bode

The α-ketoacid–hydroxylamine (KAHA) ligation allows the coupling of unprotected peptide segments. The most widely used variant employs a 5-membered cyclic hydroxylamine that forms a homoserine ester as the primary ligation product. While very effective, monomers that give canonical amino acid residues are in high demand. In order to preserve the stability and reactivity of cyclic hydroxylamines, but form a canonical amino acid residue upon ligation, we sought to prepare cyclic derivatives of serine hydroxylamine. An evaluation of several cyclization strategies led to cyclobutanone ketals as the leading structures. The preparation, stability, and amide-forming ligation of these serine-derived ketals are described.


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