Reactivity of Aromatic o-Hydroxy Oximes. II. The Use of Esters of Aromatic o-Hydroxy Oximes in Peptide Synthesis

Abstract

Esters of N-protected amino acids with o-hydroxybenzaldehyde oxime, o-hydroxyacetophenone oxime, o-hydroxybenzophenone oxime, and their 5-Cl and 5-NO2 derivatives were prepared by several methods. Various dipeptide derivatives with high purity were obtained in good yield by use of these active ester reagents.

Spiro Heterocycles: Synthesis and Application of Spiro Pyrazol-3-one Derivatives

“…84 They are also an important class of biologically useful compounds for the synthesis of fragrances 85 and therapeutic studies, 86 and useful building blocks in peptide synthesis. 87 In addition, oxime esters are selective covalent inhibitors of serine hydrolase retinoblastoma-binding protein 9 (RBBP9) 88 and cleave DNA under photolytic conditions. 89 Hence, their synthesis continues to attract attention and provides an interesting challenge.…”

Synthesis of dipeptides from N-hydroxy-3-azaspiro[5,5]undecane-2,4-dione activated α-amino acids

“…Entries 9, 12 and 15 in the table are new dipeptides, which are hitherto unreported. Their structure is established by mass, 1 H NMR, 13 C NMR and infra red spectra. The 13 C NMR has peaks at 169, 165 and 156 ppm, respectively for the newly formed peptide carbonyl carbon, respectively.…”

“…It can be noticed from Table 1 that HOASUD activation is comparable with the N-OSU method. The Boc-L-Tyr-Gly-OEt a 75 New +3.3(MeOH) e -a New peptides fully characterized by 1 H NMR, 13 enantiomeric purity was measured by optical rotatory dispersion (ORD) and compared with standard samples. 18 It has been found that the dipeptide formation occurred with complete preservation of stereochemistry.…”

A Convenient Practical Synthesis of Alkyl and Aryl Oxime Esters

“…3 They are useful building blocks in peptide synthesis. 4 Oxime esters are selective covalent inhibitors of serine hydrolase retinoblastoma-binding protein 9 (RBBP9) and cleave DNA under photolytic conditions. 5,6 They also possess fungicidal, 7 herbicidal, 8 insecticidal, 9 and antitumor activity.…”