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Synthesis and Peptidyl Group Migration in Isopropylidene Acetals Derived from the Glucose-substituted Imidazolidinone Related to Opioid Peptide Leucine-enkephalin

Maja Roščić ; Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, P. O. Box 180, 10002 Zagreb, Croatia
Štefica Horvat ; Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, P. O. Box 180, 10002 Zagreb, Croatia

Puni tekst: engleski, pdf (89 KB) str. 773-780 preuzimanja: 118* citiraj
APA 6th Edition
Roščić, M. i Horvat, Š. (2000). Synthesis and Peptidyl Group Migration in Isopropylidene Acetals Derived from the Glucose-substituted Imidazolidinone Related to Opioid Peptide Leucine-enkephalin. Croatica Chemica Acta, 73 (3), 773-780. Preuzeto s https://hrcak.srce.hr/132016
MLA 8th Edition
Roščić, Maja i Štefica Horvat. "Synthesis and Peptidyl Group Migration in Isopropylidene Acetals Derived from the Glucose-substituted Imidazolidinone Related to Opioid Peptide Leucine-enkephalin." Croatica Chemica Acta, vol. 73, br. 3, 2000, str. 773-780. https://hrcak.srce.hr/132016. Citirano 23.09.2020.
Chicago 17th Edition
Roščić, Maja i Štefica Horvat. "Synthesis and Peptidyl Group Migration in Isopropylidene Acetals Derived from the Glucose-substituted Imidazolidinone Related to Opioid Peptide Leucine-enkephalin." Croatica Chemica Acta 73, br. 3 (2000): 773-780. https://hrcak.srce.hr/132016
Harvard
Roščić, M., i Horvat, Š. (2000). 'Synthesis and Peptidyl Group Migration in Isopropylidene Acetals Derived from the Glucose-substituted Imidazolidinone Related to Opioid Peptide Leucine-enkephalin', Croatica Chemica Acta, 73(3), str. 773-780. Preuzeto s: https://hrcak.srce.hr/132016 (Datum pristupa: 23.09.2020.)
Vancouver
Roščić M, Horvat Š. Synthesis and Peptidyl Group Migration in Isopropylidene Acetals Derived from the Glucose-substituted Imidazolidinone Related to Opioid Peptide Leucine-enkephalin. Croatica Chemica Acta [Internet]. 2000 [pristupljeno 23.09.2020.];73(3):773-780. Dostupno na: https://hrcak.srce.hr/132016
IEEE
M. Roščić i Š. Horvat, "Synthesis and Peptidyl Group Migration in Isopropylidene Acetals Derived from the Glucose-substituted Imidazolidinone Related to Opioid Peptide Leucine-enkephalin", Croatica Chemica Acta, vol.73, br. 3, str. 773-780, 2000. [Online]. Dostupno na: https://hrcak.srce.hr/132016. [Citirano: 23.09.2020.]

Sažetak
The reaction of the glucose-substituted imidazolidinone 1, structurally related to endogenous opioid pentapeptide leucine-enkephalin (Tyr-Gly-Gly-Phe-Leu), with acetone in the presence of acid catalyst gives 2,3-O-isopropylidene derivative 2 along with the isomeric monoacetal 3. Evidence is presented by using RP HPLC and NMR spectroscopy that, under the conditions of ketal formation, the peptidyl group migrated from the primary (2) to the adjacent secondary hydroxy group of the sugar moiety to give ester 3. The product distribution in the equilibrated reaction mixture (2 : 3 ≈ 1.5 : 1) indicated that 5-O-peptidyl derivative 2 is slightly more stable than ester 3. Peptidyl group migration in aqueous solution at pH = 5 shows slow 23 rearrangement and markedly faster 32 conversion.

Ključne riječi
opioid; peptide; enkephalin; imidazolidinone; acetal; glucose

Hrčak ID: 132016

URI
https://hrcak.srce.hr/132016

Posjeta: 224 *