Synthesis of 9-O-Acetyl- and 4,9-Di-O-Acetyl Derivatives of the Methyl Ester of N-Acetyl-β-D-Neuraminic Acid Methylglycoside. Their Use as Models in Periodate Oxidation Studies
Publication type: Journal Article
Publication date: 1975-01-01
SJR: —
CiteScore: —
Impact factor: —
ISSN: 00184888
PubMed ID:
174994
Biochemistry
Abstract
Reaction of the methyl ester of N-acetyl-beta-D-neuraminic acid methyl glycoside with N-acetylimidazole yielded the corresponding 9-O-acetyl- and 4,9-di-O-acetyl derivatives. The structures of these compounds were confirmed by mass spectrometry and both 1H and 13C NMR spectroscopy. The compounds served as model substances in a comparative study of the rate of periodate oxidation of unsubstituted and of 9-O-acetylated-N-acetyl-neuraminic acids. This reaction was strongly hampered by the presence of the 9-O-acetyl group. The low molar absorbancy coefficient of N-acetyl-9-O-acetylneuraminic acid in the periodic acid/thiobarbituric acid assay can be explained by this retardation.
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75
Total citations:
75
Citations from 2024:
0
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GOST
Copy
Haverkamp J. et al. Synthesis of 9-O-Acetyl- and 4,9-Di-O-Acetyl Derivatives of the Methyl Ester of N-Acetyl-β-D-Neuraminic Acid Methylglycoside. Their Use as Models in Periodate Oxidation Studies // Hoppe-Seyler´s Zeitschrift für physiologische Chemie. 1975. Vol. 356. No. 2. pp. 1575-1584.
GOST all authors (up to 50)
Copy
Haverkamp J., SCHAUER R., Wember M., Kamerling J. P., VLIEGENTHART J. F. G. Synthesis of 9-O-Acetyl- and 4,9-Di-O-Acetyl Derivatives of the Methyl Ester of N-Acetyl-β-D-Neuraminic Acid Methylglycoside. Their Use as Models in Periodate Oxidation Studies // Hoppe-Seyler´s Zeitschrift für physiologische Chemie. 1975. Vol. 356. No. 2. pp. 1575-1584.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1515/bchm2.1975.356.2.1575
UR - https://doi.org/10.1515/bchm2.1975.356.2.1575
TI - Synthesis of 9-O-Acetyl- and 4,9-Di-O-Acetyl Derivatives of the Methyl Ester of N-Acetyl-β-D-Neuraminic Acid Methylglycoside. Their Use as Models in Periodate Oxidation Studies
T2 - Hoppe-Seyler´s Zeitschrift für physiologische Chemie
AU - Haverkamp, Johan
AU - SCHAUER, ROLAND
AU - Wember, Margret
AU - Kamerling, Johannis P
AU - VLIEGENTHART, JOHANNES F. G.
PY - 1975
DA - 1975/01/01
PB - Walter de Gruyter
SP - 1575-1584
IS - 2
VL - 356
PMID - 174994
SN - 0018-4888
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{1975_Haverkamp,
author = {Johan Haverkamp and ROLAND SCHAUER and Margret Wember and Johannis P Kamerling and JOHANNES F. G. VLIEGENTHART},
title = {Synthesis of 9-O-Acetyl- and 4,9-Di-O-Acetyl Derivatives of the Methyl Ester of N-Acetyl-β-D-Neuraminic Acid Methylglycoside. Their Use as Models in Periodate Oxidation Studies},
journal = {Hoppe-Seyler´s Zeitschrift für physiologische Chemie},
year = {1975},
volume = {356},
publisher = {Walter de Gruyter},
month = {jan},
url = {https://doi.org/10.1515/bchm2.1975.356.2.1575},
number = {2},
pages = {1575--1584},
doi = {10.1515/bchm2.1975.356.2.1575}
}
Cite this
MLA
Copy
Haverkamp, Johan, et al. “Synthesis of 9-O-Acetyl- and 4,9-Di-O-Acetyl Derivatives of the Methyl Ester of N-Acetyl-β-D-Neuraminic Acid Methylglycoside. Their Use as Models in Periodate Oxidation Studies.” Hoppe-Seyler´s Zeitschrift für physiologische Chemie, vol. 356, no. 2, Jan. 1975, pp. 1575-1584. https://doi.org/10.1515/bchm2.1975.356.2.1575.