Protecting group free synthesis of glycosyl thiols from reducing sugars in water; application to the production of N-glycan glycoconjugates.

Expedient synthesis of an α-S-(1→6)-linked pentaglucosyl thiol.

An α-S-(1→6)-linked pentaglucosyl thiol has been synthesized in a convenient and stereoselective way. Key steps of the synthesis involved thioglycosylation of 6-iodinated sugars with α-glycosyl thiols under phase transfer conditions. The α-configuration of glycosidic linkages was thus introduced prior to the coupling steps, and relied on the intrinsic configurational stability of α-glycosyl thi...

Developmental Changes of the Notochord and its Inductive Effects on the Adjacent Embryonic Germ Layers with Regard to the Role of Glycoconjugates

Notochord is an axial structure derived of embryonic mesoderm and in addition to structural supporting role in inducing nearby germinal layers, it has a basic role in formation of organs such as vertebral column, axial vessels, neural tube and primitive gut. This organ undergoes essential changes during the development process. First, arises from the primitive node and terms notochordal process...

The direct formation of glycosyl thiols from reducing sugars allows one-pot protein glycoconjugation.

A coordinated synthesis and conjugation strategy for the preparation of homogeneous glycoconjugate vaccine candidates.

Glycoconjugates are the center of many therapeutic strategies and carbohydrate-based vaccines in particular hold great promise. The development of glycovaccines, however, can be hindered by the limited access offered by natural sources to homogeneous antigenic carbohydrates; efficient chemical synthesis offers an attractive route to pure samples of these carbohydrates. Furthermore, for an optim...

Synthetic and semi-synthetic approaches to unprotected N-glycan oxazolines

N-Glycan oxazolines have found widespread use as activated donor substrates for endo-β-N-acetylglucosaminidase (ENGase) enzymes, an important application that has correspondingly stimulated interest in their production, both by total synthesis and by semi-synthesis using oligosaccharides isolated from natural sources. Amongst the many synthetic approaches reported, the majority rely on the fabr...