A New Route for Preparation of 5‐Deoxy‐5‐(hydroxyphosphinyl)‐D‐mannopyranose and ‐L‐gulopyranose Derivatives.

Hanaya, Tadashi; Yamamoto, Hiroshi

doi:10.1002/chin.200301197

Cited by 1 publication

(2 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Hanaya with his team have dedicated an intense activity to the development of new methods to introduce of a phosphinyl group into the sugar skeleton, especially for the preparation of d ‐mannopyranose phosphasugar analogues 91 and 92 (Figure ) …”

Section: Endocyclic Oxygen Replacementmentioning

confidence: 99%

See 1 more Smart Citation

Design and synthesis of glycomimetics: Recent advances

Tamburrini

Colombo

Bernardi

2019

Medicinal Research Reviews

View full text Add to dashboard Cite

In the past few decades, our understanding of glycan information‐encoding power has notably increased, thus leading to a significant growth also in the design and synthesis of glycomimetic probes. Combining data from multiple analytical sources, such as crystallography, nuclear magnetic resonance spectroscopy, and other biophysical methods (eg, surface plasmon resonance and carbohydrate microarrays) has allowed to shed light on the key interaction events between carbohydrates and their protein‐targets. However, the low metabolic stability of carbohydrates and their high hydrophilicity, which translates in low bioavailability, undermine their development as drugs. In this framework, the design of chemically modified analogues (called carbohydrate mimics or glycomimetics) appears as a valid alternative for the development of therapeutic agents. Glycomimetics, as structural and functional mimics of carbohydrates, can replace the native ligands in the interaction with target proteins, but are designed to show enhanced enzymatic stability and bioavailability and, possibly, an improved affinity and selectivity toward the target. In the present account, we specifically focus on the most recent advances in the design and synthesis of glycomimetics. In particular, we highlight the efforts of the scientific community in the development of straightforward synthetic procedures for the preparation of sugar mimics and in their preliminary biological evaluation.

show abstract

Section: Endocyclic Oxygen Replacementmentioning

confidence: 99%

“…The phosphonyl group was introduced as dimethyl‐phosphonate, in the presence of DBU, on the key intermediate 93 (Figure ) . After a few standard manipulations, compounds 94a ‐ b were converted into the corresponding penta‐acetates 91 and 92 .…”

Section: Endocyclic Oxygen Replacementmentioning

confidence: 99%