Useful hydroxylamine derivatives for the synthesis of hydroxamic acids.

Design of Peptide Hydroxamate‐Based Photoreactive Activity‐Based Probes of Zinc‐Dependent Metalloproteases

“…Selective acidic removal of the tert-butyl group gave carboxylic acid 17 which was transformed into fully protected succinyl hydroxamate 18 by first transformation into the corresponding acyl chloride and next reaction with the lithiate of N-Boc-O-TBS-hydroxylamine. [40] We previously found [32] that condensation of N-Boc-O-TBS-hydroxylamine with related acyl chlorides proceeded well under the agency of two equivalents of 4-dimethylaminopyridine (DMAP) as the base. However, this procedure proved less efficient in the transformation aimed for here, and optimal results were obtained by adding dropwise the lithiate of N-Boc-O-TBS-hydroxylamine to a THF solution of the acyl chloride.…”

Synthesis of New Glycerolipids Linked to Hydroxamate Derivatives Designed for Two‐Dimensional Crystallization of Aminopeptidase M

“…Commonly used methods for the synthesis of hydroxamic acids are the direct acylation of hydroxylamine with various acylating reagents, such as carboxylic acid chlorides or activated esters (cf. [6] and ref. cit.…”

“…The aminopeptidase M can be reversibly inhibited by several classes of compounds, including commercially available peptides, for example bestatin or amastatin [5]. However, much simpler structures such as nonpeptidic hydroxamic acids exhibit comparable affinity towards this metalloprotease [6].…”

“…Due to the amphiphilic behavior of compounds l,, we did not succeed in determining accurate affinity constants for the AP-M. However, substitution of the 1,3-dioleyl-glycerol moiety by a PhCH, group leads to a water-soluble compound which could be tested and displays competitive inhibition towards AP-M in the same range as bestatin (K, M [6]). Moreover, omission of the i-Bu chain decreases the affinity by two orders of magnitude.…”

Facile Synthesis of N α -Protected Amino/Peptide Hydroxamic Acids Mediated by COMU

“…The reported methods for the preparation of hydroxamic acids include the reaction of O/N-protected hydroxylamines with activated carboxylic acids (Tamaki et al 1993;Altenburger et al 1992;Ando and Tsumaki 1983;Lee and Miller 1983;Anilkumar et al 2000). Coupling of carboxylic acids with hydroxylamine in presence of cyanuric chloride (TCT) (Giacomelli et al 2003) and cyclic phosphonic anhydride (PPAA or T3P) (Ech-Chahad et al 2005;Basavaprabhu et al 2013) require longer duration (6-12 h) for completion.…”