Synthesis of heteroglycoclusters by using orthogonal chemoselective ligations

• Baptiste Thomas,
• Michele Fiore,
• Isabelle Bossu,
• Pascal Dumy and
• Olivier Renaudet

Beilstein J. Org. Chem. 2012, 8, 421–427, doi:10.3762/bjoc.8.47

• using a single coupling reaction. By contrast, the chemical access of heteroglycoclusters is not trivial because it requires the controlled conjugation of different sugars at a precise position into the scaffold to obtain a well-defined distribution. Taking advantage of our experience in bioconjugation

The allylic chalcogen effect in olefin metathesis

• Yuya A. Lin and
• Benjamin G. Davis

Beilstein J. Org. Chem. 2010, 6, 1219–1228, doi:10.3762/bjoc.6.140

• metathesis has been further exploited in protein modifications. This is discussed next. Applications in protein modifications For the potential use of olefin metathesis in bioconjugation, the genetic incorporation of alkene containing amino acid residues has been well documented [18][40][41][42][43][44

• develop olefin metathesis as a more general method for bioconjugation, we have considered various key factors including steric, electronic and allyl linker selection in substrates that contribute to successful CM on proteins (Scheme 13) [38]. These studies suggest that an unhindered allyl sulfide or

• reaction itself. We hope to see this concept being further exploited in bioconjugation and synthetic chemistry. Allylic hydroxy activation in RCM [19]. Possible complexes generated through preassociation of allylic alcohol with ruthenium. a) Variation of olefin metathesis: CM = cross-metathesis; RCM = ring

Kinetic studies and predictions on the hydrolysis and aminolysis of esters of 2-S-phosphorylacetates

• Milena Trmčić and
• David R. W. Hodgson

Beilstein J. Org. Chem. 2010, 6, 732–741, doi:10.3762/bjoc.6.87

• organic synthesis. Aminolysis of reactive esters in aqueous systems is often used in bioconjugation chemistry, but it must compete against hydrolysis processes. Here we study the kinetics of aminolysis and hydrolysis of 2-S-phosphorylacetate ester intermediates that result from displacement of bromide by

• nucleophile are present at comparable concentrations. The concentrations of reagents in most synthetic laboratory reactions are usually ~0.01–0.05 M with one reagent being present in slight excess. Under standard conditions for bioconjugation processes, these concentrations are usually significantly lower and

Synthesis of coumarin or ferrocene labeled nucleosides via Staudinger ligation

• Ivana Kosiova,
• Andrea Janicova and
• Pavol Kois

Beilstein J. Org. Chem. 2006, 2, No. 23, doi:10.1186/1860-5397-2-23

• gives iminophosphoranes which can react with almost any kind of electrophilic reagent, e.g. aldehydes/ketones to form imines or esters to form amides. This so-called Staudinger ligation has been employed in a wide range of applications as a general tool for bioconjugation including specific labeling of

• electrophiles, such as esters, can undergo reaction with iminophosphorane to form amides, especially if the electrophilic attack proceeds in an intramolecular fashion. [17][18][19][20][21] This so-called Staudinger ligation has been employed in a wide range of applications as a general tool for bioconjugation