Sucrose analogs: an attractive (bio)source for glycodiversification

Abstract

Sucrose is a widespread carbohydrate in nature and is involved in many biological processes. Its natural abundance makes it a very appealing renewable raw material for the synthetic production of high-valued molecules. To further diversify the structure and the inherent properties of these molecules, the access to sucrose analogs is of utmost interest and has historically been widely explored through chemical means. Nature also offers a large panel of sucrose-scaffold derivatives, including phosphorylated or highly substituted phenylpropanoid esters amenable to transformation. Additionally, the use of microorganisms or enzymes could provide an alternative ecologicallycompatible manner to diversify sucrose-scaffold derivatives to enable the synthesis of oligo-or polysaccharides, glycoconjugates or polymers that could exhibit original properties for biotechnological applications. This review covers the main biological routes to sucrose derivatives or analogs that are prevalent in nature, that can be obtained via enzymatic processes and the potential applications of such sucrose derivatives in sugar bioconversion, in particular through the engineering of substrates, enzymes or microorganisms.

Recent novel applications of levansucrases

“…Inulin-type fructan is used by some plants as a means of storing energy. However, microorganisms prefer to produce levan-type fructan as an energy reserve (Daude et al 2012) and as an important structural component for defense (Benigar et al 2014). Therefore, the levan-producing enzyme, levansucrase occurs in a wide range of microorganisms.…”

Probing Substrate Promiscuity of Amylosucrase from Neisseria polysaccharea

“…[17] Nevertheless, sucrose derivatives could constitute a renewable attractive biosource for glycodiversification and increase the number of accessible glycoconjugates through the catalysis of promiscuous sucrose-utilizing enzymes, as first proposed by Buchholz and co-workers who also investigated the promiscuity of GH family 70 enzymes towards alternate acceptors. [18][19][20][21][22][23] Until recently, the 3 D structure of Neisseria polysaccharea amylosucrase (NpAS) was the only available structure of an amylosucrase. [24][25][26][27] With the determination of the X-ray crystallographic structure of the thermostable amylosucrase from Deinococcus geothermalis, [28] there has been a new wealth of structural information to better understand substrate and product specificities of amylosucrase.…”

Levansucrases of a Pseudomonas syringae pathovar as catalysts for the synthesis of potentially prebiotic oligo- and polysaccharides

“…1), levansucrases produce polymeric levan, DP of which can be very high, even over 100,000 [45]. The first reaction of levan synthesis is formation of 6-kestose from two Substrates and oligosaccharidic products of levansucrases (adapted in a modified form from [58] with permission from the publisher). Sucrose, raffinose and stachyose act as fructosyl donors as well as acceptors for levansucrases, whereas 1-kestose, 6-kestose, neokestose, blastose and levan-type FOS are produced in the reaction with sucrose as the substrate.…”

“…In neokestose (belongs to neo-FOS; DP 3; Fig. 1), b-2,6 linkage joins the fructose and glucose residues [57,58]. Neo-FOS are produced also from sucrose by several fungal (e.g.…”