Triazole: the Keystone in Glycosylated Molecular Architectures Constructed by a Click Reaction
Tóm tắt
The copper(I)‐catalyzed modern version of the Huisgen‐type azide–alkyne cycloaddition to give a 1,4‐disubstituted 1,2,3‐triazole unit is introduced as a powerful ligation method for glycoconjugation. Owing to its high chemoselectivity and tolerance of a variety of reaction conditions, this highly atom‐economic and efficient coupling reaction is especially useful for the effective construction of complex glycosylated structures such as clusters, dendrimers, polymers, peptides, and macrocycles. In all cases the triazole ring plays a key role by locking into position the various parts of these molecular architectures. The examples reported and briefly discussed in this short review highlight the use of this reaction in carbohydrate chemistry and pave the way to further developments and applications.
Từ khóa
Tài liệu tham khảo
Nobel Lectures:
Almost 600 papers have been published since 2002 the year of the discovery of the copper(I) catalysis (personal communication by K. B. Sharpless).
Lwowski W., 1984, 1,3‐Dipolar Cycloaddition Chemistry, Vol. 1, 559
In architecture the keystone is the central wedge‐shaped block of an arch that locks its parts together. The semicircular arch was present in Etruscan structures around 700 BC and was then developed by the Romans in the vaults and domes of their monumental buildings.
1999, Essentials of Glycobiology
2003, Carbohydrate‐Based Drug Discovery, Vol. 1 and 2
For reviews see:
Postema M. H. D., 1995, C‐Glycoside Synthesis
The problem of the unequivocal assignment of the triazole regiochemistry in complex systems and with a single isomer in hand is addressed in reference [26c].
Fürstner A., J. Org. Chem., 8, 63