- Arginine thioacid in synthesis of arginine conjugates and peptides
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Protected arginine thioacid enables convenient N-acylation with no detectable racemization. We report efficient syntheses of potentially biologically active arginine conjugates and novel arginine-containing di-, tri- and tetrapeptides in good yields witho
- Khaybullin, Ravil N.,Panda, Siva S.,Mirzai, Saeid,Toneff, Ellen,Asiri, Abdullah M.,Hall, C. Dennis,Katritzky, Alan R.
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p. 55210 - 55216
(2015/01/09)
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- Efficient synthesis of peptides by extension at the N- and C-terminii of arginine
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(Chemical Equation Presented) L-Nω-Nitroarginine and L-arginine were coupled with N-(Cbz-α-aminoacyl)benzotriazoles and N-Cbz-dipeptidoylbenzotriazoles to provide arginine LL-dipeptides 9a-e, 11a-d; LLL-tripeptides 18a-c, 20; and diastereomeric mixtures (9b+9b′), (9c+9c′), (11b+11b′) and (18c+18c′) [compound numbers written within parentheses represent a diastereomeric mixture or racemate; compound numbers without parentheses represent an achiral compound or a single enantiomer] by extension at the N-terminus of arginine, in isolated yields of 66-95% with complete retention of chirality as evidenced by NMR and HPLC analysis. Arginine LL-dipeptides 15a-d were synthesized by extension at the C-terminus of arginine in isolated yield of 66-80%, using benzotriazole activated arginine L-ωNO2-Arg-Bt, 13. Our methodology has also been used to synthesize the protected RGD peptide (Cbz α-L-ωNO2-Arg-Gly-L-Asp-(OH) 2) 21.
- Katritzky, Alan R.,Meher, Geeta,Narindoshvili, Tamari
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p. 7153 - 7158
(2009/05/07)
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- Studies of Bitter Peptides from Casein Hydrolyzate. I. Synthesis of Bitter Peptide BPIa Corresponding to Arg-Gly-Pro-Pro-Phe-Ile-Val from Casein Hydrolyzate by Alkaline Proteinase of Bacillus subtilis
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A bitter heptapeptide BPIa was synthesized and compared with the natural peptide, isolated by Minamiura et al. from casein hydrolyzate, by means of thin layer chromatography, paper electrophoresis, and carboxymethylcellulose column chromatography.All resu
- Fukui, Hiroshi,Kanehisa, Hidenori,Ishibashi, Norio,Miyake, Ichizo,Okai, Hideo
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p. 766 - 769
(2007/10/02)
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