Azides in Carbohydrate Chemistry

Beckmann, Henning S. G.; Wittmann, Valentin

doi:10.1002/9780470682517.ch16

“…It is well established that aromatic azides are an important class of compounds having various interesting applications in organic chemistry [9–11] as well as material science [12–15] and drug discovery [16–18]. Organic azides in general are popular in recent times because of their use as synthons in Cu(I)-catalyzed “click chemistry” [19].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and DNA interaction studies of new triptycene derivatives

Chakraborty¹,

Mondal²,

Kumari³

et al. 2014

Beilstein J. Org. Chem.

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SummaryA facile and efficient synthesis of a new series of triptycene-based tripods is being reported. Using 2,6,14- or 2,7,14-triaminotriptycenes as synthons, the corresponding triazidotriptycenes were prepared in high yield. Additionally, we report the transformation of 2,6,14- or 2,7,14-triaminotriptycenes to the corresponding ethynyl-substituted triptycenes via their tribromo derivatives. Subsequently, derivatization of ethynyl-substituted triptycenes was studied to yield the respective propiolic acid and ethynylphosphine derivatives. Characterization of the newly functionalized triptycene derivatives and their regioisomers were carried out using FTIR and multinuclear NMR spectroscopy, mass spectrometry, and elemental analyses techniques. The study of the interaction of these trisubstituted triptycenes with various forms of DNA revealed interesting dependency on the functional groups of the triptycene core to initiate damage or conformational changes in DNA.

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“…Besides the 2-azidoethyl linker, a 6-azidohexyl linker was also used in anomeric functionalization. The higher C to N ratio made the 6-azidohexyl linker a safer choice compared to its two carbon counterpart [ 76 , 77 ].…”

Section: Stereoselective Anomeric Functionalization For Chemical Cmentioning

confidence: 99%

Anomeric O-Functionalization of Carbohydrates for Chemical Conjugation to Vaccine Constructs

Park

¹

,

Hsieh

²

,

Gervay‐Hague

³

2018

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Carbohydrates mediate a wide range of biological interactions, and understanding these processes benefits the development of new therapeutics. Isolating sufficient quantities of glycoconjugates from biological samples remains a significant challenge. With advances in chemical and enzymatic carbohydrate synthesis, the availability of complex carbohydrates is increasing and developing methods for stereoselective conjugation these polar head groups to proteins and lipids is critically important for pharmaceutical applications. The aim of this review is to provide an overview of commonly employed strategies for installing a functionalized linker at the anomeric position as well as examples of further transformations that have successfully led to glycoconjugation to vaccine constructs for biological evaluation as carbohydrate-based therapeutics.

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“…Besides the 2-azidoethyl linker, a 6-azidohexyl linker was also used in anomeric functionalization. The higher C to N ratio made the 6-azidohexyl linker a safer choice compared to its two carbon counterpart [75,76]. [80].…”

Section: Anomeric Functionalization With Terminal Azido Linkersmentioning

confidence: 99%

Anomeric Functionalization of Carbohydrates for Chemical Conjugation to Vaccine Constructs

Gervay‐Hague¹,

Park²,

Hsieh³

2018

Preprint

0

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Carbohydrates mediate a wide range of biological interactions, and understanding these processes benefits the development of new therapeutics. Isolating sufficient quantities of glycoconjugates from biological samples remains a significant challenge. With advances in chemical and enzymatic carbohydrate synthesis, the availability of complex carbohydrates is increasing and developing methods for stereoselective conjugation these polar head groups to proteins and lipids is critically important for pharmaceutical applications. The aim of this review is to provide an overview of commonly employed strategies for installing a functionalized linker at the anomeric position as well as examples of further transformations that have successfully led to glycoconjugation to vaccine constructs for biological evaluation as carbohydrate-based therapeutics.

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Azides in Carbohydrate Chemistry

Cited by 17 publications

References 180 publications

Synthesis, characterization and DNA interaction studies of new triptycene derivatives

Synthesis, characterization and DNA interaction studies of new triptycene derivatives

Anomeric O-Functionalization of Carbohydrates for Chemical Conjugation to Vaccine Constructs

Anomeric Functionalization of Carbohydrates for Chemical Conjugation to Vaccine Constructs

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