Synthesis and CD spectra in MeCN, MeOH, and H2O of γ-oligopeptides with hydroxy groups on the backbone was written by Brenner, Meinrad;Seebach, Dieter. And the article was included in Helvetica Chimica Acta in 2001.Name: 1-((3aS,6R,7aR)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)prop-2-en-1-one This article mentions the following:
γ4-Tripeptides and γ4-hexapeptides, I [n = 1, 2; R1 = Boc (Boc = tert-butoxycarbonyl), R2 = Bn;] and II (n = 1, 2; R1 = Boc, R2 = Bn, or n = 2, R1 = R2 = H) with OH groups in the 2- or 3-position on each residue have been prepared The corresponding 2-hydroxy amino acids were obtained by Si-nitronate (3+2) cycloadditions to the acryloyl derivative of Oppolzer’s sultam and Raney-Ni reduction of the resulting 1,2-oxazolidines. The 3-hydroxy amino acid derivatives were prepared by chain elongation via Claisen condensation of Boc-Ala-OH, Boc-Val-OH, and Boc-Leu-OH, and NaBH4 reduction of the Me 4-amino 3-oxo carboxylates formed. The N-Boc hydroxy amino acids were coupled in solution to give the γ-peptides. CD spectra of the new types of γ-peptides were recorded and compared with those of simple γ2-, γ3-, γ4-, and γ2,3,4-peptides. An intense Cotton effect at ca. 200 nm ([Θ]= -2.105 deg·cm2·dmol-1) indicates that the hexapeptide built of (3R,4S)-4-amino-3-hydroxy acids (with the side chains of Val, Ala, Leu) folds to a secondary structure so far unknown. The stability of peptides from β- and γ-amino acids, which carry heteroatoms on their backbones is discussed. Positions on the γ-peptidic 2.614 helix are identified at which non-H-atoms are “allowed”. In the experiment, the researchers used many compounds, for example, 1-((3aS,6R,7aR)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)prop-2-en-1-one (cas: 94594-91-9Name: 1-((3aS,6R,7aR)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)prop-2-en-1-one).
1-((3aS,6R,7aR)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)prop-2-en-1-one (cas: 94594-91-9) belongs to isothiazole derivatives. Similar to other five-membered heterocycles, isothiazoles react with a wide range of electrophilic and nucleophilic reagents to form diverse products. Various penicillins and cephalosporins having an isothiazole ring system have shown considerable antibacterial efficacy against Gram-positive and Gram-negative bacteria.Name: 1-((3aS,6R,7aR)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)prop-2-en-1-one
Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com