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  • The Journal of Physical Chemistry B.
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Further manipulation of terminal alkenyl linkers can be achieved through various conditions [ 60 ] Figure 6. The double bond functionality can be transformed to the corresponding thioether via radical reaction using thiol derivatives. Oxidative cleavage using NaIO 4 with RuCl 3 and OsO 4 yield the corresponding carboxylic acid and aldehyde which are readily available for ester bond formation, Wittig-type reaction, and reductive amination. Ozonolysis followed by hydroboration-oxidation can also be applied to alkenyl linker, leading to the corresponding alcohol.

Ozonolysis and reductive amination were employed in the preparation of Globo H conjugates. Globo H was isolated in by the Hakomori group [ 61 ]. The tumor-associated carbohydrate antigen TACA can be found overexpressed in breast, pancreas, small bowel, ovarian and prostate cancer [ 62 ]; therefore, it has been a valuable synthetic target toward novel therapeutic development. Isolating globo H from biological samples is challenging and typically limited to sub-milligram quantities. On the other hand, chemical synthesis has enabled large-scale production of homogenous and pure oligosaccharides in larger scale.

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The Danishefsky group has led efforts toward fully synthetic carbohydrate-based anticancer vaccine development [ 63 , 64 ]. In the first generation of globo H total synthesis, the hexasaccharide was assembled via glycal chemistry, leaving a glycal functionality at the reducing end Figure 7.

The protected globo H glycal was subsequently reacted with dimethyldioxirane DMDO followed by solvolysis with allylic alcohol. The epoxide ring opening glycosylation reaction proceeded in good yield with b-selective incorporation of the alkenyl linker. However, this functionality did not survive the subsequent deprotection step using the Birch reduction. The crude reaction mixture contained mainly glycosidic bond cleavage products and fragmentation of the hexasaccharide [ 65 , 66 , 67 ]. To avoid these complications, the globo H glycal was deprotected and then reprotected as a per- O -acetylated trisaccharide prior to the DMDO reaction.

Ozonolysis of the alkene followed by reductive amination with the KLH carrier protein, gave a fully synthetic carbohydrate vaccine for the immunology investigations Figure 7. The group also developed a second-generation total synthesis of globo H by introducing a 4-pentenyl linker at an early stage of the lactosyl building block preparation Figure 8. In , the Bundle group developed a non-immunologenic triethylene oxide linker equipped with an NHS ester on one end and an alkenyl functional group on the other [ 68 ].

The glycoconjugate linker retained an alkenyl handle that could be further reacted with a sulfhydryl group of a peptide construct containing the specific T H peptide epitope pm in high yields. More recently, the Cairo group employed thio-alkenylation conjugation chemistry to construct multivalent ABO blood group glycoconjugates [ 69 ] on a PEGylated scaffold.

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The design for generating tetravalent or trivalent forms of ABO blood glycoconjugates was based on various conjugation chemical strategies. It first started with an octenyl lactoside, which was converted to an amine under photo-induced radical addition of cysteamine hydrochloride. The first group of the amine-terminated glycan was reacted with the NHS ester of the linker followed by the removal of NHFmoc to expose an amine, which was reacted with the PEG scaffold.

Essentials of carbohydrate chemistry / John F. Robyt. - Version details - Trove

An extension of the conjugation chemistry with deprotected glycans explored by the Bundle group was applied to a heterotrifunctional linker to generate a large, complex glycoconjugate in a controlled manner in good yields. This work was a more straightforward approach than the earlier work by the Buriak group, which demonstrated the feasibility of conjugating p -nitrophenyl functionalized glycan antigens on silica microparticles albeit in lower molecular size [ 70 ].

With careful manipulation of the bio-orthogonal functional groups available on a robust, non-immunologenic linker, large glycotopes could be synthesized in pure forms. In general, terminal alkene linkers, especially the n pentenyl linker, have been popular in the carbohydrate chemistry community since the late to s. While thiolinker was first introduced to study glycosylation reactions, it later proved to be a versatile functional group for total synthesis of complex glycans equipped with a functionalizable linker.

One drawback of the linker is the electron-rich nature of the double bond functionality. It does not survive strongly acidic conditions, Lewis acid-abundant environments, radical reactions or hydrogenation, which limits the use of certain reagents during oligosaccharide syntheses.