Glycosidic cleavage from anaerobic saponification of the heptaacetate of daunomycin hydroquinone

1993 ◽  
Vol 115 (13) ◽  
pp. 5446-5452 ◽  
Author(s):  
Barbara Ann Schweitzer ◽  
Tad H. Koch
Keyword(s):  
Glycosidic Cleavage

Pulse radiolysis study of daunorubicin redox reactions: Redox cycles or glycosidic cleavage?

1986 ◽  
Vol 2 (2) ◽  
pp. 89-97
Author(s):  
C HOUEELEVIN ◽  
M GARDESALBERT ◽  
C FERRADINI
Keyword(s):  
Redox Reactions ◽  
Pulse Radiolysis ◽  
Glycosidic Cleavage ◽  
Redox Cycles

Mechanistic understanding of cellulose β-1,4-glycosidic cleavage via photocatalysis

2021 ◽  
pp. 120872
Author(s):  
Heng Zhao ◽  
Chao-Fan Li ◽  
Xinti Yu ◽  
Na Zhong ◽  
Zhi-Yi Hu ◽  
...  
Keyword(s):  
Glycosidic Cleavage ◽  
Mechanistic Understanding

ChemInform Abstract: Glycosidic Cleavage from Anaerobic Saponification of the Heptaacetate of Daunomycin Hydroquinone.

ChemInform ◽  
2010 ◽  
Vol 24 (44) ◽  
pp. no-no
Author(s):  
B. A. SCHWEITZER ◽  
T. H. KOCH
Keyword(s):  
Glycosidic Cleavage

PROPOSED MECHANISM FOR THE REDUCTIVE GLYCOSIDIC CLEAVAGE OF DAUNOMYCIN (NSC 82151) AND ADRIAMYCIN (NSC 123127)

1977 ◽  
pp. 688-697 ◽  
Author(s):  
David W. Yesair ◽  
Suzanne McNitt ◽  
Linda Bittman
Keyword(s):  
Glycosidic Cleavage

Microscale glycosidic cleavage of oligosaccharide bromobenzoates for circular dichroism analysis

1989 ◽  
Vol 111 (24) ◽  
pp. 8944-8946 ◽  
Author(s):  
Makoto Ojika ◽  
Harold V. Meyers ◽  
Mayland Chang ◽  
Koji Nakanishi
Keyword(s):  
Circular Dichroism ◽  
Glycosidic Cleavage ◽  
Circular Dichroism Analysis ◽  
Circular Dichroïsm

Gas phase glycosidic cleavage of oxynions from alkyl glycosides

1987 ◽  
Vol 22 (1) ◽  
pp. 6-12 ◽  
Author(s):  
Jean-Claude Prome ◽  
Hélène Aurelle ◽  
Danielle Prome ◽  
Arlette Savagnac
Keyword(s):  
Gas Phase ◽  
Alkyl Glycosides ◽  
Glycosidic Cleavage

scholarly journals A MECHANISM FOR THE ANOMERIZATION OF ACETYLATED ALKYL GLYCOPYRANOSIDES

1955 ◽  
Vol 33 (1) ◽  
pp. 120-127 ◽  
Author(s):  
R. U. Lemieux ◽  
W. P. Shyluk
Keyword(s):  
Boron Trifluoride ◽  
Titanium Tetrachloride ◽  
Ion Pair ◽  
Methoxyl Group ◽  
Racemic Mixture ◽  
Unsuccessful Attempt ◽  
Glycosidic Cleavage ◽  
Carbon 14 ◽  
Intramolecular Mechanism

Unequivocal evidence that the anomerization of acetylated alkyl glycopyranosides can proceed by way of an intramolecular mechanism was obtained through the observation that a racemic mixture of methyl β-glucopyranoside tetraacetate with the D-isomer labelled in the methoxyl group with carbon-14 is anomerized both by titanium tetrachloride and boron trifluoride without transfer of radioactive methoxyl groups to the L-isomer. It is submitted that these intramolecular anomerizations are best rationalized as the result of an unsuccessful attempt by the environment to bring about glycosidic cleavage and proceed by way of an ion-pair intermediate in which the anion is derived from the aglycon group.

scholarly journals Metabolism of 4-n-Nonylphenol by Non-modified and CYP1A1- and CYP1A2-Transgenic Cell Cultures of Tobacco

2005 ◽  
Vol 60 (11-12) ◽  
pp. 883-892 ◽  
Author(s):  
Angelika Berger ◽  
Alexander S. Ruß ◽  
Ingolf Schuphan ◽  
Burkhard Schmidt
Keyword(s):  
Cell Suspension Cultures ◽  
Oxidative Capacity ◽  
Side Chain ◽  
Phase System ◽  
Metabolic Profiles ◽  
Hydrolytic Cleavage ◽  
Primary Metabolites ◽  
Glycosidic Cleavage ◽  
Transgenic Cell ◽  
Human Cytochrome

The metabolism of 14C-4-n-nonylphenol (14C-4-n-NP), as a mo-el for the xenoestrogen nonylphenol, was investigate- in three types of tobacco cell suspension cultures: one genetically non-modified culture (NT) and two cultures constitutively expressing human cytochrome P450 CYP1A1 or CYP1A2. With 1 mg l-1 of 14C-4-n-NP and 24 h of incubation, the xenobiotic was transformed almost completely to glycosides. After glycosidic cleavage, 14C-4-n-NP and several primary metabolites of 14C-4-n-NP were liberated. Portions of the primary metabolites were 29.3% (NT culture), 34.3% (CYP1A1 culture), and 50.7% of applied 14C(CYP1A2 culture). Thus, the endogenous capacity of the tobacco cells to form primary metabolites of 4-n-NP was noticeably higher than that of CYP1A1 or CYP1A2. The results however clearly suggest that 4-n-NP is - even though a poor - substrate of CYP1A1 an- CYP1A2. In order to examine metabolic profiles of 4-n-NP in the NT, CYP1A1 and CYP1A2 cultures, the suspensions were exposed to 10 mg l-1 of 14C-4-n-NP using a two-liquid-phase system with carrier n-hexadecane and 192 h of incubation. Results obtained resembled those of the low concentration study. The oxidative metabolic profiles determined after hydrolytic cleavage using GC-EIMS were similar in the NT, CYP1A1 and CYP1A2 cultures. Main metabolites were side-chain mono-hydroxylated derivatives of 4-n-NP with 6′-, 7′- and 8′- OH-4-n-NP as prominent metabolites. In addition, olefinic side-chain hydroxy, ring methoxylated, keto and ring hydroxylated derivatives were observed. The lack of differences in metabolic profiles among the CYP1A1, CYP1A2 and NT cultures was referred to the low enzymatic activity of CYP1A1 and CYP1A2 as compared to the higher endogenous oxidative capacity of tobacco, as well as to similar metabolic profiles of 4-n-NP produced by CYP1A1 and CYP1A2 an- tobacco itself.

scholarly journals Mechanism of Human α-1,3-Fucosyltransferase V:  Glycosidic Cleavage Occurs Prior to Nucleophilic Attack†

Biochemistry ◽  
1997 ◽  
Vol 36 (4) ◽  
pp. 823-831 ◽  
Author(s):  
Brion W. Murray ◽  
Valentin Wittmann ◽  
Michael D. Burkart ◽  
Shang-Cheng Hung ◽  
Chi-Huey Wong
Keyword(s):  
Nucleophilic Attack ◽  
Glycosidic Cleavage
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