Carbohydrate–steroid conjugation by Ugi reaction: one-pot synthesis of triple sugar/pseudo-peptide/spirostane hybrids

Rivera, Daniel G.; Pérez-Labrada, Karell; Lambert, Liudmila; Dörner, Simon; Westermann, Bernhard; Wessjohann, Ludger A.

doi:10.1016/j.carres.2012.05.003

Cited by 26 publications

(17 citation statements)

References 83 publications

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“…From the various reports that employ steroids in Ugi‐4CRs,28 we are aware of only two examples that make use of isocyanosteroids14b, 28a and another two that use aminosteroids 14b. 28d However, those groups were attached either to the flexible side or to the steroidal nucleus with an equatorial orientation, thereby lacking the reactivity problems usually found in steroid chemistry with axial substituents.…”

Section: Resultsmentioning

confidence: 99%

A Multiple Multicomponent Approach to Chimeric Peptide–Peptoid Podands

Rivera

León

Concepción

et al. 2013

Chemistry A European J

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The success of multi-armed, peptide-based receptors in supramolecular chemistry traditionally is not only based on the sequence but equally on an appropriate positioning of various peptidic chains to create a multivalent array of binding elements. As a faster, more versatile and alternative access toward (pseudo)peptidic receptors, a new approach based on multiple Ugi four-component reactions (Ugi-4CR) is proposed as a means of simultaneously incorporating several binding and catalytic elements into organizing scaffolds. By employing α-amino acids either as the amino or acid components of the Ugi-4CRs, this multiple multicomponent process allows for the one-pot assembly of podands bearing chimeric peptide-peptoid chains as appended arms. Tripodal, bowl-shaped, and concave polyfunctional skeletons are employed as topologically varied platforms for positioning the multiple peptidic chains formed by Ugi-4CRs. In a similar approach, steroidal building blocks with several axially-oriented isocyano groups are synthesized and utilized to align the chimeric chains with conformational constrains, thus providing an alternative to the classical peptido-steroidal receptors. The branched and hybrid peptide-peptoid appendages allow new possibilities for both rational design and combinatorial production of synthetic receptors. The concept is also expandable to other multicomponent reactions.

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Section: Resultsmentioning

confidence: 99%

A Multiple Multicomponent Approach to Chimeric Peptide–Peptoid Podands

Rivera

León

Concepción

et al. 2013

Chemistry A European J

Self Cite

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“…The final product incorporates all atoms from the four reactants, except that one water molecule. Ugi reactions have been employed to prepare sugar-based hybrids (Rivera et al, 2012), and exploited for their potential to prepare glycoconjugate vaccines (Mendez et al, 2018). The Ugi reaction has been employed to conjugate two different polysaccharidic antigens to one carrier protein in a single step (Mendez et al, 2018).…”

Section: Other Methodsmentioning

confidence: 99%

Chemical synthesis of polysaccharide–protein and polysaccharide–peptide conjugates: A review

Zhou

Petrova

Edgar

2021

Carbohydrate Polymers

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“…95 The multicomponent approach as a tool to achieve carbohydrate-steroid conjugation has also been validated recently, again by exploration of the formidably versatile Ugi reaction. 96 In fact, sugar-based inputs have been studied intensively in Ugi condensations in the attempt to devise stereoselective versions of this important reaction but successful examples are still scarce. 97 On the other hand, reliable ways to induce diastereoselectivity in the Petasis 3CR reaction were not as intricate to develop, and sugars as well as other renewable feedstocks have found utility in this respect.…”

Section: Renewable Feedstocksmentioning

confidence: 99%