Linear Synthesis of the Tumor‐Associated Carbohydrate Antigens Globo‐H, SSEA‐3, and Gb3.

Boße, Folkert; Marcaurelle, Lisa A.; Seeberger, Peter H.

doi:10.1002/chin.200306184

Cited by 4 publications

(4 citation statements)

References 2 publications

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“…22,25,533−537 The biological importance of the Globo-H antigen is so widespread throughout the scientific community that many synthetic approaches have been developed. [63][64][65][66]68 Seeberger and co-workers also developed reaction conditions to achieve β-mannosylation on a solid phase using an automated approach. 538 They started from the methodology developed by Crich 539 involving 4,6-O-benzylidene-protected mannosyl donors bearing a sulfoxide leaving group.…”

Section: Peptide Synthesizer-based Automationmentioning

confidence: 99%

Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges

et al. 2018

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Advances in carbohydrate chemistry have certainly made common oligosaccharides much more accessible. However, many current methods still rely heavily upon specialized knowledge of carbohydrate chemistry. The application of automated technologies to chemical and life science applications such as genomics and proteomics represents a vibrant field. These automated technologies also present opportunities for their application to organic synthesis, including that of the synthesis of oligosaccharides. However, application of automated methods to the synthesis of carbohydrates is an underdeveloped area as compared to other classes of biomolecules. The overarching goal of this review article is to present the advances that have been made at the interface of carbohydrate chemistry and automated technology.

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Section: Peptide Synthesizer-based Automationmentioning

confidence: 99%

Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges

et al. 2018

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“…The n-4-pentenyl linker not only functionalized the anomeric position, but also served as a leaving group under the activation of proper promoters [52]. The dual property of the linker was found very useful in traditional total synthesis of oligosaccharides published by the same group [53,54] (Table 1, entry 6).…”

Section: Anomeric Functionalization With Terminal Alkenyl Linkersmentioning

confidence: 99%

Anomeric Functionalization of Carbohydrates for Chemical Conjugation to Vaccine Constructs

Gervay‐Hague¹,

Park²,

Hsieh³

2018

Preprint

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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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“…137 Synthetic access to antigens of the Globo series has been accelerated using new methods. [138][139][140][141] Automated synthesis delivered Globo-H and Gb3 in about 1 day. 42 Six building blocks were required for the synthesis of the fully protected Globo-H hexasaccharide (82-87, Scheme 13).…”

Section: Anticancer Vaccinesmentioning

confidence: 99%

Carbohydrates: A Frontier in Medicinal Chemistry

et al. 2009

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Linear Synthesis of the Tumor‐Associated Carbohydrate Antigens Globo‐H, SSEA‐3, and Gb3.

Cited by 4 publications

References 2 publications

Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges

Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges

Anomeric Functionalization of Carbohydrates for Chemical Conjugation to Vaccine Constructs

Carbohydrates: A Frontier in Medicinal Chemistry

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