Highly reactive “RIKEN click” probe for glycoconjugation on lysines

Sibgatullina, Regina; Fujiki, Katsumasa; Murase, Takefumi; Yamamoto, Takahiro; Shimoda, Taiji; Kurbangalieva, Almira; Tanaka, Katsunori

doi:10.1016/j.tetlet.2017.03.081

Cited by 17 publications

(4 citation statements)

References 26 publications

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“…However, the synthesis of the key intermediate 1 containing dibenzocyclooctyne and unsaturated aldehyde fragments (Figure 1) is very complicated and time consuming [38]. In their research, Tanaka et al always seek to improve the synthetic methodology [49,50]. Thus, at first, it was suggested to replace compound 1 with the similar unsaturated aldehyde 7a (Figure 8), which can be easily obtained from the commercially available carboxylic acid in three steps [49].…”

Section: Arbitrarily Arranged Heterogeneous Glycoalbuminsmentioning

confidence: 99%

“…In their research, Tanaka et al always seek to improve the synthetic methodology [49,50]. Thus, at first, it was suggested to replace compound 1 with the similar unsaturated aldehyde 7a (Figure 8), which can be easily obtained from the commercially available carboxylic acid in three steps [49]. It was shown that the new key intermediate 7a is more reactive in the terms of both click reactions and could be successfully used in the synthesis of various glycoalbumins [44].…”

Section: Arbitrarily Arranged Heterogeneous Glycoalbuminsmentioning

confidence: 99%

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Homo- and Heterogeneous Glycoconjugates on the Basis of N-Glycans and Human Serum Albumin: Synthesis and Biological Evaluation

et al. 2022

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Neoglycoconjugates mimicking natural compounds and possessing a variety of biological functions are very successful tools for researchers to understand the general mechanisms of many biological processes in living organisms. These substances are characterized by high biotolerance and specificity, with low toxicity. Due to the difficult isolation of individual glycoclusters from biological objects, special interest has been directed toward synthetic analogs. This review is mainly focused on the one-pot, double-click methodology (containing alkyne–azide click cycloaddition with the following 6π-azaelectrocyclization reactions) used in the synthesis of N-glycoconjugates. Homogeneous (including one type of biantennary N-glycan fragments) and heterogeneous (containing two to four types of biantennary N-glycan fragments) glycoclusters on albumin were synthesized via this strategy. A series of cell-, tissue- and animal-based experiments proved glycoclusters to be a very promising class of targeted delivery systems. Depending on the oligosaccharide units combined in the cluster, their amount, and arrangement relative to one another, conjugates can recognize various cells, including cancer cells, with high selectivity. These results open new perspectives for affected tissue visualization and treatment.

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Section: Arbitrarily Arranged Heterogeneous Glycoalbuminsmentioning

confidence: 99%

Section: Arbitrarily Arranged Heterogeneous Glycoalbuminsmentioning

confidence: 99%

Homo- and Heterogeneous Glycoconjugates on the Basis of N-Glycans and Human Serum Albumin: Synthesis and Biological Evaluation

et al. 2022

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“…Alternatively, when a haloacetylated sugar chain derivative is reacted with a thiol-containing peptide, a glycan can be introduced selectively at the Cys residue (Method B). Recently, in addition to the above two methods, the use of the 6π-azaelectrocyclization (RIKEN-CLICK reaction) developed by Tanaka et al has made it possible to add glycans to Lys residues (19). By using the thereby obtained homogeneous glycopeptide as a segment and performing native chemical ligation, it is possible to synthesize a homogeneous glycoprotein.…”

Section: Organic Synthesis Of Glycoproteinsmentioning

confidence: 99%

Biopharmaceutical Discovery by Organic Synthesis

Asai

Ochiai

Elouali

2017

TIGG

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Glycoprotein drugs have a remarkable structural complexity among biopharmaceuticals. The main reason for this is the diversity and complexity of their glycans. We have become able to prepare, in high-purity and large quantities, glycans which are extremely difficult to artificially control with posttranslational modification. We have also established a method of adding uniform glycans to arbitrary positions. These technologies make it possible to prepare homogeneous glycoproteins that are extremely difficult to prepare by expression. In addition, because glycans can be introduced to new arbitrary positions, appropriate design of the position, number, and structure of these sugar chains has made it possible to create next-generation biopharmaceuticals.

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“…A terminal aldehyde functionalized N -glycan was prepared, through formation of 1,2,3-triazole by strain-promoted azide-alkyne click reaction. Aldehyde functionality was subjected to reaction with lysine residues of albumin, which subsequently underwent the 6π-electrocyclization to form conjugated enamine ( Scheme 12D ) (Sibgatullina et al, 2017 ).…”

Section: Introductionmentioning

confidence: 99%

Glycoconjugations of Biomolecules by Chemical Methods

Sarkar

Jayaraman

2020

Front. Chem.

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Bioconjugations under benign aqueous conditions have the most promise to covalently link carbohydrates onto chosen molecular and macromolecular scaffolds. Chemical methodologies relying on C-C and C-heteroatom bond formations are the methods of choice, coupled with the reaction conditions being under aqueous milieu. A number of methods, including metal-mediated, as well as metal-free azide-alkyne cyclo-addition, photocatalyzed thiol-ene reaction, amidation, reductive amination, disulfide bond formation, conjugate addition, nucleophilic addition to vinyl sulfones and vinyl sulfoxides, native chemical ligation, Staudinger ligation, olefin metathesis, and Suzuki-Miyaura cross coupling reactions have been developed, in efforts to conduct glycoconjugation of chosen molecular and biomolecular structures. Within these, many methods require pre-functionalization of the scaffolds, whereas methods that do not require such pre-functionalization continue to be few and far between. The compilation covers synthetic methodology development for carbohydrate conjugation onto biomolecular and biomacromolecular scaffolds. The importance of such glycoconjugations on the functional properties is also covered.

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Highly reactive “RIKEN click” probe for glycoconjugation on lysines

Cited by 17 publications

References 26 publications

Homo- and Heterogeneous Glycoconjugates on the Basis of N-Glycans and Human Serum Albumin: Synthesis and Biological Evaluation

Homo- and Heterogeneous Glycoconjugates on the Basis of N-Glycans and Human Serum Albumin: Synthesis and Biological Evaluation

Biopharmaceutical Discovery by Organic Synthesis

Glycoconjugations of Biomolecules by Chemical Methods

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