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. 2021 Feb 23;38(1):101–117. doi: 10.1007/s10719-021-09974-y

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© The Author(s) 2021

Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/.

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Fig. 2 — OligoGM1 synthesis strategies. a Scheme of the chemical synthesis of OligoGM1. GM1 undergoes to ozonolytic (O₃) process in methanol (i) generating a desphingosine aldehyde product and a miristic aldehyde (ii), followed by alkaline hydrolysis in triethylamine (Et₃N) (iii) releasing OlgoGM1; b Scheme of the chemical synthesis of tritium-labeled and photoactivable OligoGM1. [³H]GM1 undergoes ozonolysis (i) in methanol followed by triethylamine alkaline hydrolysis (ii) releasing [³H]OligoGM1. The latter is subjected to the amination process (iii) and the [³H]OligoGM1-NH₂ is azide labeled (iv) with 2-nitro-fluorophenylazide in dimethylformamide (DMF) and tributiylamine (Bu₃N) in dimethylsulfoxide (DMSO) to obtain [³H]OligoGM1-N₃. c OligoGM1 biosynthesis in engineered Escherichia coli. Lactose and sialic acid (Neu5Ac) are internalized by the specific permeases LacY and NanT but cannot be degraded because of β-galactosidase (LacZ) and aldolase (NanA) deletion. CMP-Neu5Ac synthase activates Neu5Ac into CMP-Neu5Ac which is transferred onto lactose by α2,3-sialyltransferase (encoded by Lst), to form II³αNeu5Ac-Lac (sialyllactose, OligoGM3). The use of the endogenous pool of UDP-GalNAc produced by the recombinant UDP-GlcNAc C4 epimerase (WbpP) allows β1,4-GalNAc transferase (CgtA) to catalyze the glycosylation of sialyllactose to form II³αNeu5Ac-Gg₃ (OligoGM2). This compound is substrate for the β1,3-galactosyltransferase (CgtB) to yield II³αNeu5Ac-Gg₄ (OligoGM1). CTP, cytidine triphosphate; Ppi, inorganic pyrophosphate. Oligosaccharide sugar code is according to Varki et al. [36]

Fig. 2 — OligoGM1 synthesis strategies. a Scheme of the chemical synthesis of OligoGM1. GM1 undergoes to ozonolytic (O₃) process in methanol (i) generating a desphingosine aldehyde product and a miristic aldehyde (ii), followed by alkaline hydrolysis in triethylamine (Et₃N) (iii) releasing OlgoGM1; b Scheme of the chemical synthesis of tritium-labeled and photoactivable OligoGM1. [³H]GM1 undergoes ozonolysis (i) in methanol followed by triethylamine alkaline hydrolysis (ii) releasing [³H]OligoGM1. The latter is subjected to the amination process (iii) and the [³H]OligoGM1-NH₂ is azide labeled (iv) with 2-nitro-fluorophenylazide in dimethylformamide (DMF) and tributiylamine (Bu₃N) in dimethylsulfoxide (DMSO) to obtain [³H]OligoGM1-N₃. c OligoGM1 biosynthesis in engineered Escherichia coli. Lactose and sialic acid (Neu5Ac) are internalized by the specific permeases LacY and NanT but cannot be degraded because of β-galactosidase (LacZ) and aldolase (NanA) deletion. CMP-Neu5Ac synthase activates Neu5Ac into CMP-Neu5Ac which is transferred onto lactose by α2,3-sialyltransferase (encoded by Lst), to form II³αNeu5Ac-Lac (sialyllactose, OligoGM3). The use of the endogenous pool of UDP-GalNAc produced by the recombinant UDP-GlcNAc C4 epimerase (WbpP) allows β1,4-GalNAc transferase (CgtA) to catalyze the glycosylation of sialyllactose to form II³αNeu5Ac-Gg₃ (OligoGM2). This compound is substrate for the β1,3-galactosyltransferase (CgtB) to yield II³αNeu5Ac-Gg₄ (OligoGM1). CTP, cytidine triphosphate; Ppi, inorganic pyrophosphate. Oligosaccharide sugar code is according to Varki et al. [36]