Modified natural substances—fluorinated and fluoroalkylated monosaccharides and inositols

Miethchen, Ralf

doi:10.1016/j.jfluchem.2004.01.015

Cited by 37 publications

(20 citation statements)

References 61 publications

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“…Stereoselective coupling of 10 with Fmoc-Thr(a-4,6-O-Bzn-GalNAc)-OtBu (7) was achieved most successfully by the Helferich method [18] with microwave assistance. Thus, on irradiation of the acceptor 7 with 6-deoxy-6-fluorogalactosyl bromide (10) and Hg(CN) 2 in MeNO 2 /CH 2 Cl 2 3:2 at 100 W (80 8C) a clean conversion into the b-configured disaccharide 17 (98 %) was observed without significant formation of orthoester or a-configured byproducts. Remarkably, conventional heating of the reaction mixture only led to diminished yields of conjugate 17, due to decomposition of the donor, although the corresponding galactosylation with the non-fluorinated donor Ac 4 GalBr [19] had proceeded smoothly even at room temperature without microwave support.…”

Section: Resultsmentioning

confidence: 97%

“…[8] Moreover, the electron-withdrawing nature of fluorine affects the reactivity of an adjacent glycosidic bond, enabling the use of fluorinated substrate analogues as mechanistic probes for glycosyl-processing enzymes and metabolic studies. [9] The strong interest in fluorinated mono-and oligosaccharides has resulted in a number of methods for their synthesis, [10] including the syntheses of mucin-like core structures. [11] In contrast, only a few pseudo-glycopeptides containing fluorinated glycosyl amino acids are available from the literature.…”

Section: Introductionmentioning

confidence: 99%

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Fluorinated Glycosyl Amino Acids for Mucin‐Like Glycopeptide Antigen Analogues

Wagner

Mersch

Hoffmann‐Röder

2010

Chemistry A European J

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The aberrant glycosylation profiles of mucin glycoproteins on epithelial tumour cells represent attractive target structures for the development of immunotherapy against cancer. Mucin-type glycopeptides have been successfully investigated as molecularly defined vaccine prototypes for triggering humoral immunity but are susceptible to rapid in vivo degradation. As a potential means to enhance the bioavailabilities of the antigenic structures, hydrolysis-resistant carbohydrate analogues with fluorine substituents at positions C6, C2' and C6' were synthesised and incorporated into the tandem repeat sequence of the mucin MUC1. The resulting pseudo-glycopeptides can be used to elucidate the effects of chemically modified antibody determinants on metabolic and immunological properties.

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Section: Resultsmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

Fluorinated Glycosyl Amino Acids for Mucin‐Like Glycopeptide Antigen Analogues

Wagner

Mersch

Hoffmann‐Röder

2010

Chemistry A European J

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“…(rel)-(1S and 1R,3S)-3-(t-Butyldimethylsilanyloxy) cyclopentanol (6). TBDMSCl (2.29 g, 15.25 mmol) was added slowly to a solution of 5 (1.41 g, 13.87 mmol) and imidazole (1.41 g, 20.80 mmol) in CH 2 Cl 2 (100 mL) at −10°C and stirred for 7 h at the same temperature.…”

Section: Methodsmentioning

confidence: 99%

“…The presence of a CF 3 group on the sugar moiety of nucleosides could confer many advantages including increased lipophilicity 6 and improved chemical and/or enzymatic stability. 7 In addition, the trifluoromethyl group can enhance the therapeutic properties of bioactive compounds.…”

Section: Although Monofluorinatedmentioning

confidence: 99%

Efficient Synthesis of Novel 4'-Trifluoromethyl-5'-norcarbocyclic Purine Phosphonic Acid Analogs by Using the Ruppert-Prakash Reaction

Kim¹,

Kim²,

Yoo³

et al. 2014

Bulletin of the Korean Chemical Society

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Novel 4'-trifluoromethyl-5'-norcarbocyclic purine phosphonic acid analogs were efficiently synthesized from commercially available 1,3-dihydroxy cyclopentane (5). Trifluoromethylation was successfully performed by using the Ruppert-Prakash reaction. The purine nucleosidic bases were efficiently coupled by using the Mitsunobu reaction. The synthesized adenosine phosphonic acids analogs 13 and 16 were screened for antiviral activity against human immunodeficiency virus-1 (HIV-1). Adenine derivative 13 exhibited significant anti-HIV-1 activity.

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“…A α-DL-difluorometil-ornitina (DFMO) (4) (6), no qual o C-24 é impedido de sofrer hidroxilação metabólica pela presença do substituinte difluorometileno, evitando assim a degradação da vitamina D 3 antes de ser absorvida pelo organismo (Figura 5). 22 O grupo difluorometileno aumenta a atividade biológica de diversos produtos naturais empregados no combate a diferentes tipos de doenças, podendose citar os análogos do 1,3-bis-fosfoglicérico (7 e 8) (Figura 6).…”

Section: Importância E Aplicações Do Grupo Difluorometilenounclassified

Importance and highlights in difluorination of organic compounds

Ferreira¹

2009

Revista Virtual De Química

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This mini-review aims to present the importance of replacement one or more fluorine atoms at C-O or C-H centers especially in the medicinal chemistry area. This bioisosteric change produces marked results and unexpected biological activity. In particular, the group difluoromethylene has been described as a bioisoster of the carbonyl function and has increased the biological activity of many compounds. The insertion of CF 2 group in organic molecules can be achieved through direct or indirect fluorination. In this paper will be described some positive examples of the introduction of the CF 2 group in medicinal chemistry and some methods used to insert it. Keywords: difluoromethylene; bioisoster; difluorination ResumoEste artigo descreve a importância da substituição de um ou mais átomos de flúor em ligações C-O ou C-H especialmente na área de química medicinal. Esta modificação bioisostérica produz resultados marcantes e inesperados na atividade biológica. Em especial, o grupo difluorometileno tem sido descrito como um bioisóstero da função carbonila e tem aumentado a atividade biológica de muitas substâncias. A inserção do grupamento CF 2 em moléculas orgânicas pode ser realizada através da fluoração direta ou indireta. Nesta minirrevisão serão abordados alguns exemplos da introdução do grupo CF 2 e alguns métodos utilizados para a sua inserção em moléculas orgânicas.

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Modified natural substances—fluorinated and fluoroalkylated monosaccharides and inositols

Cited by 37 publications

References 61 publications

Fluorinated Glycosyl Amino Acids for Mucin‐Like Glycopeptide Antigen Analogues

Fluorinated Glycosyl Amino Acids for Mucin‐Like Glycopeptide Antigen Analogues

Efficient Synthesis of Novel 4'-Trifluoromethyl-5'-norcarbocyclic Purine Phosphonic Acid Analogs by Using the Ruppert-Prakash Reaction

Importance and highlights in difluorination of organic compounds

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