Chemoenzymatic synthesis of neoglycoproteins driven by the assessment of protein surface reactivity

Bavaro, Teodora; Filice, Marco; Temporini, Caterina; Tengattini, Sara; Serra, Immacolata; Morelli, Carlo F.; Massolini, Gabriella; Terreni, Marco

doi:10.1039/c4ra11131a

Cited by 26 publications

(40 citation statements)

References 26 publications

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“…Lysine has been traditionally and most widely used for the modification of proteins because of the presence of primary amines 1,3 and a number of reactions are possible, including reactions with activated esters, sulfonyl chlorides, isothiocyanates, 2-amino-2-methoxyethyl (IME) 20,21 and squaric acids, 22 as well as reductive alkylation using aldehydes in the presence of sodium borocyanohydride (Fig. 2).…”

Section: •1 Lysinementioning

confidence: 99%

Recent Progress in Chemical Modification of Proteins

Sakamoto

Hamachi

2018

ANAL. SCI.

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Chemical modification of proteins is important for creating a myriad of engineered proteins and for elucidating the function and dynamics of proteins in live cells. A wide variety of chemical protein modification methods have been developed and can be categorized into three classes: (i) modification of proteins using the reactivity of naturally occurring amino acids; (ii) modification by bioorthogonal reactions using unnatural amino acids, most of which can be siteselectively incorporated into proteins-of-interest using genetic codon expansion techniques; and (iii) recognition driven chemical modification, which is the only approach that allows modification of endogenous proteins without any genetic manipulation even under heavily crowded and multi-molecular conditions, as in live cells and organisms. All of these approaches have merits and limitations. In this review, we summarize these approaches and discuss their characteristics with respect to specificity, reaction rate and versatility.

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Section: •1 Lysinementioning

confidence: 99%

Recent Progress in Chemical Modification of Proteins

Sakamoto

Hamachi

2018

ANAL. SCI.

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“…Firstly, the sialic acid was activated as the sialyl xanthate form based on the previous report [17]. Then the mannose bearing a free 6-OH residue M1 was obtained by enzymatic hydrolysis according to the reported method [18,19]. In this study, we introduced enzymatic hydrolysis to prepare GM3 building block M1, which can avoid multiple chemical procedures.…”

Section: Synthesis Of Gm3 Analoguesmentioning

confidence: 99%

Chemoenzymatically synthesized ganglioside GM3 analogues with inhibitory effects on tumor cell growth and migration

Zheng¹,

Guan

Liu

et al. 2019

European Journal of Medicinal Chemistry

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Ganglioside GM3, belonging to glycosphingolipid family, has been known as tumor-associated carbohydrate antigen on several types of tumor. Many studies have revealed that GM3 plays a role in cell proliferation, adhesion and differentiation, which is crucial in the process of cancer development. In the present study, we firstly synthesized novel mannose containing GM3 analogues by enzymatic hydrolysis and chemical procedures. Then the antiproliferative activity of the novel analogues along with galactose containing analogues we prepared previously was investigated and the data demonstrated that these analogues exhibited antiproliferative effect on K562 and HCT116 cells. Finally, the influence of these analogues on tumor cell migration was studied on B16, B16-F10 and HCCLM3 cells by wound healing test, because the migration of tumor cells represents one of the relevant factors in assessing the malignancy of cancer. This study could lay the foundation for optimizing leading compounds and provide valuable information for finding new antitumor drugs for cancer therapy.

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“…The biocatalytic use of enzymes provides the possibility to develop efficient processes with low environmental impact in several fields ranging from pharma to food [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16]. Nowadays, covalent immobilization of enzymes [17][18][19] is increasingly used to improve operational performances, to ensure the recovery and the reuse of the biocatalysts and to avoid contamination of the final product with residual proteins [20][21][22].…”

Section: Introductionmentioning

confidence: 99%

Developing a Novel Enzyme Immobilization Process by Activation of Epoxy Carriers with Glucosamine for Pharmaceutical and Food Applications

et al. 2019

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In this paper, we describe the development of an efficient enzyme immobilization procedure based on the activation of epoxy carriers with glucosamine. This approach aims at both creating a hydrophilic microenvironment surrounding the biocatalyst and introducing a spacer bearing an aldehyde group for covalent attachment. First, the immobilization study was carried out using penicillin G acylase (PGA) from Escherichia coli as a model enzyme. PGA immobilized on glucosamine activated supports has been compared with enzyme derivatives obtained by direct immobilization on the same non-modified carriers, in the synthesis of different 3′-functionalized cephalosporins. The derivatives prepared by immobilization of PGA on the glucosamine-carriers performed better than those prepared using the unmodified carriers (i.e., 90% versus 79% cefazolin conversion). The same immobilization method has been then applied to the immobilization of two other hydrolases (neutral protease from Bacillus subtilis, PN, and bromelain from pineapple stem, BR) and one transferase (γ-glutamyl transpeptidase from Bacillus subtilis, GGT). Immobilized PN and BR have been exploited in the synthesis of modified nucleosides and in a bench-scale packed-bed reactor for the protein stabilization of a Sauvignon blanc wine, respectively. In addition, in these cases, the new enzyme derivatives provided improved results compared to those previously described.

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Chemoenzymatic synthesis of neoglycoproteins driven by the assessment of protein surface reactivity

Cited by 26 publications

References 26 publications

Recent Progress in Chemical Modification of Proteins

Recent Progress in Chemical Modification of Proteins

Chemoenzymatically synthesized ganglioside GM3 analogues with inhibitory effects on tumor cell growth and migration

Developing a Novel Enzyme Immobilization Process by Activation of Epoxy Carriers with Glucosamine for Pharmaceutical and Food Applications

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