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Literature DB >> 31749363

Chemical Synthesis of Human Milk Oligosaccharides: Lacto-N-hexaose Galβ1→3GlcNAcβ1→3 [Galβ1→4GlcNAcβ1→6] Galβ1→4Glc.

Mithila D Bandara¹, Keith J Stine¹, Alexei V Demchenko¹.

Abstract

The first synthesis of lacto-N-hexaose (LNH) has been completed using a convergent strategy. The donor-acceptor protecting-leaving group combinations were found to be of paramount significance for achieving successful glycosylations and minimizing side reactions. Lacto-N-tetraose, another common human milk oligosaccharide, was also obtained en route to the target LNH.

Entities: CellLine Chemical Disease Gene Species

Mesh：

Substances：
Oligosaccharides

Year: 2019 PMID： 31749363 PMCID： PMC8114087 DOI： 10.1021/acs.joc.9b02701

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

25 in total

1. Synthesis of lacto-N-tetraose.

Authors: Kelly M Craft; Steven D Townsend
Journal: Carbohydr Res Date: 2017-02-11 Impact factor: 2.104

Review 2. Breast milk oligosaccharides: structure-function relationships in the neonate.

Authors: Jennifer T Smilowitz; Carlito B Lebrilla; David A Mills; J Bruce German; Samara L Freeman
Journal: Annu Rev Nutr Date: 2014-05-15 Impact factor: 11.848

3. Fast pyrolysis of 13C-labeled cellobioses: gaining insights into the mechanisms of fast pyrolysis of carbohydrates.

Authors: John C Degenstein; Priya Murria; Mckay Easton; Huaming Sheng; Matt Hurt; Alex R Dow; Jinshan Gao; John J Nash; Rakesh Agrawal; W Nicholas Delgass; Fabio H Ribeiro; Hilkka I Kenttämaa
Journal: J Org Chem Date: 2015-01-22 Impact factor: 4.354

Review 4. The Human Milk Glycome as a Defense Against Infectious Diseases: Rationale, Challenges, and Opportunities.

Authors: Kelly M Craft; Steven D Townsend
Journal: ACS Infect Dis Date: 2017-11-15 Impact factor: 5.084

Review 5. Human milk oligosaccharides and infant gut bifidobacteria: Molecular strategies for their utilization.

Authors: Pamela Thomson; Daniel A Medina; Daniel Garrido
Journal: Food Microbiol Date: 2017-09-04 Impact factor: 5.516

6. Characterization of lacto-N-hexaose and two fucosylated derivatives from human milk by high-performance liquid chromatography and proton NMR spectroscopy.

Authors: V K Dua; K Goso; V E Dube; C A Bush
Journal: J Chromatogr Date: 1985-06-28

Review 7. Structure-function relationships of human milk oligosaccharides.

Authors: Lars Bode; Evelyn Jantscher-Krenn
Journal: Adv Nutr Date: 2012-05-01 Impact factor: 8.701

8. Production of human milk oligosaccharides by enzymatic and whole-cell microbial biotransformations.

Authors: Georg A Sprenger; Florian Baumgärtner; Christoph Albermann
Journal: J Biotechnol Date: 2017-07-29 Impact factor: 3.307

Review 9. Human Milk Oligosaccharides (HMOS): Structure, Function, and Enzyme-Catalyzed Synthesis.

Authors: Xi Chen
Journal: Adv Carbohydr Chem Biochem Date: 2015-11-11 Impact factor: 3.714

Review 10. Human Milk Oligosaccharides: 2'-Fucosyllactose (2'-FL) and Lacto-N-Neotetraose (LNnT) in Infant Formula.

Authors: Yvan Vandenplas; Bernard Berger; Virgilio Paolo Carnielli; Janusz Ksiazyk; Hanna Lagström; Manuel Sanchez Luna; Nathalia Migacheva; Jean-Marc Mosselmans; Jean-Charles Picaud; Mike Possner; Atul Singhal; Martin Wabitsch
Journal: Nutrients Date: 2018-08-24 Impact factor: 5.717

4 in total