Synthesis and antifungal activity of pradimicin derivatives. Modifications of the sugar part.

Aburaki, Shimpei; Yamashita, Haruhiro; Ohnuma, Takeshi; Kamachi, Hajime; Moriyama, Toshio; Masuyoshi, Shinji; Kamei, Hideo; Konishi, Masataka; Oki, Taikan

doi:10.7164/antibiotics.46.631

Cited by 15 publications

(12 citation statements)

References 12 publications

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“…The 4-deoxy-4-fluoro-D-fucoside D-2b was then obtained by two further protecting group manipulations. 60 DAST fluorination was attempted on the D-quinovose derivative 14 (Scheme 1c) but afforded none of the expected 4-deoxy-4-fluorofucoside 17. Instead, a very low yield of the quinovose derivative 15 was obtained, with 5-fluoroaltrofuranoside 16 as the major product.…”

Section: ■ Introductionmentioning

confidence: 99%

Synthesis and Structural Characteristics of all Mono- and Difluorinated 4,6-Dideoxy-d-xylo-hexopyranoses

et al. 2021

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Protein–carbohydrate interactions are implicated in many biochemical/biological processes that are fundamental to life and to human health. Fluorinated carbohydrate analogues play an important role in the study of these interactions and find application as probes in chemical biology and as drugs/diagnostics in medicine. The availability and/or efficient synthesis of a wide variety of fluorinated carbohydrates is thus of great interest. Here, we report a detailed study on the synthesis of monosaccharides in which the hydroxy groups at their 4- and 6-positions are replaced by all possible mono- and difluorinated motifs. Minimization of protecting group use was a key aim. It was found that introducing electronegative substituents, either as protecting groups or as deoxygenation intermediates, was generally beneficial for increasing deoxyfluorination yields. A detailed structural study of this set of analogues demonstrated that dideoxygenation/fluorination at the 4,6-positions caused very little distortion both in the solid state and in aqueous solution. Unexpected trends in α/β anomeric ratios were identified. Increasing fluorine content always increased the α/β ratio, with very little difference between regio- or stereoisomers, except when 4,6-difluorinated.

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Section: ■ Introductionmentioning

confidence: 99%

Synthesis and Structural Characteristics of all Mono- and Difluorinated 4,6-Dideoxy-d-xylo-hexopyranoses

et al. 2021

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“…Similar spectroscopic data were reported in the 1-0-glucoside derivative of PRML. 4) Halogenation of PRMA with pyridinium bromide perbromide (Py-HBr3) or I2 -Nal -NaOH gave different two types of substitution products, 4-bromo (3) and 10-iodo (4) derivatives ofPRM A, respectively, whose structures were determined by comparative NMR analysis of the aromatic protons as shown in Scheme1. These results suggested that substitution reactions such as halogenation occurred at 4-position under acidic conditions and at 10-position under alkaline conditions.…”

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confidence: 99%

Synthesis and antifungal activity of pradimicin derivatives. Modifications on the aglycone part.

et al. 1993

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“…This is consistent with the previous reports on the analogues of the aglycon pradimicinone, which further confirmed that the sugar moieties are essential for the biological activities of pradimicins. [21, 22] …”

Section: Resultsmentioning

confidence: 99%

Synergistic Actions of Tailoring Enzymes in Pradimicin Biosynthesis

et al. 2014

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Three key tailoring enzymes PdmJ, PdmW and PdmN in pradimicin biosynthesis were investigated. PdmW was characterized as the C-6 hydroxylase by structural characterization of the corresponding product 6-hydroxy-G-2A. The efficiencies of the C-5 and C-6 hydroxylations catalyzed respectively by PdmJ and PdmW were low when they were expressed individually with the early biosynthetic enzymes that form G-2A. When these two cytochrome P450 enzymes were co-expressed, a dihydroxylated product 5,6-dihydroxy-G-2A was efficiently produced, indicating that these two enzymes work synergistically in pradimicin biosynthesis. Heterologously expressed PdmN in Streptomyces coelicolor CH999 converted G-2A to JX137a by ligating a unit of D-alanine to the carboxyl group. PdmN has relaxed substrate specificity toward both amino acid donors and acceptors. Through combinatorial biosynthesis, a series of new pradimicin analogues were produced.

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Synthesis and antifungal activity of pradimicin derivatives. Modifications of the sugar part.

Cited by 15 publications

References 12 publications

Synthesis and Structural Characteristics of all Mono- and Difluorinated 4,6-Dideoxy-d-xylo-hexopyranoses

Synthesis and Structural Characteristics of all Mono- and Difluorinated 4,6-Dideoxy-d-xylo-hexopyranoses

Synthesis and antifungal activity of pradimicin derivatives. Modifications on the aglycone part.

Synergistic Actions of Tailoring Enzymes in Pradimicin Biosynthesis

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