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Literature DB >> 22342206

Glycosylation of α-amino acids by sugar acetate donors with InBr3. Minimally competent Lewis acids.

Mark R Lefever¹, Lajos Z Szabò, Bobbi Anglin, Michael Ferracane, Joanna Hogan, Lauren Cooney, Robin Polt.

Abstract

A simplified method for the preparation of Fmoc-serine and Fmoc-threonine glycosides for use in O-linked glycopeptide synthesis is described. Lewis acids promote glycoside formation, but also promote undesired reactions of the glycoside products. Use of 'minimally competent' Lewis acids such as InBr(3) promotes the desired activation catalytically, and with greatly reduced side products from sugar peracetates.

Entities: Chemical Gene Species

Mesh：

Substances：

Year: 2012 PMID： 22342206 PMCID： PMC3296895 DOI： 10.1016/j.carres.2012.01.008

Source DB: PubMed Journal: Carbohydr Res ISSN： 0008-6215 Impact factor: 2.104

11 in total

1. Lewis base activation of Lewis acids: catalytic enantioselective allylation and propargylation of aldehydes.

Authors: S E Denmark; T Wynn
Journal: J Am Chem Soc Date: 2001-06-27 Impact factor: 15.419

2. Concerning the origin of the high beta-selectivity of glycosidation reactions of 2-deoxy-2-iodo-glucopyranosyl trichloroacetimidates.

Authors: Pek Y Chong; William R Roush
Journal: Org Lett Date: 2002-12-12 Impact factor: 6.005

3. Lewis base activation of Lewis acids: catalytic, enantioselective addition of silyl ketene acetals to aldehydes.

Authors: Scott E Denmark; Gregory L Beutner; Thomas Wynn; Martin D Eastgate
Journal: J Am Chem Soc Date: 2005-03-23 Impact factor: 15.419

4. Facile synthesis of glycosylated Fmoc amino acid building blocks assisted by microwave irradiation.

Authors: Nianhuan Yao; Gabriel Fung; Hamed Malekan; Long Ye; Mark J Kurth; Kit S Lam
Journal: Carbohydr Res Date: 2010-08-02 Impact factor: 2.104

5. Microwave-assisted glycosylation for the synthesis of glycopeptides.

Authors: Jürgen Seibel; Lars Hillringhaus; Roxana Moraru
Journal: Carbohydr Res Date: 2005-02-28 Impact factor: 2.104

6. Solid-phase synthesis of O-linked glycopeptide analogues of enkephalin.

Authors: S A Mitchell; M R Pratt; V J Hruby; R Polt
Journal: J Org Chem Date: 2001-04-06 Impact factor: 4.354

7. [Synthesis of xylose-containing glycopeptides that contain the amino acid sequence 4 bis 7 des NH2-terminus of the protein core structure of cattle skin proteodermatan sulfates].

Authors: H G Garg; T Hasenkamp; H Paulsen
Journal: Carbohydr Res Date: 1986-08-15 Impact factor: 2.104

8. Stereoselective synthesis of beta-D-glycopyranosyl-L-serinate or -threoninate derivatives with an unusual migration.

Authors: L Szabó; R Polt
Journal: Carbohydr Res Date: 1994-05-20 Impact factor: 2.104

9. FeCl3-catalyzed alpha-glycosidation of glycosamine pentaacetates.

Authors: Guohua Wei; Xun Lv; Yuguo Du
Journal: Carbohydr Res Date: 2008-09-09 Impact factor: 2.104

10. Synthesis of the glycosyl amino acids N alpha-Fmoc-Ser[Ac4-beta-D-Galp-(1-->3)-Ac2-alpha-D-GalN3p]-OPfp and N alpha-Fmoc-Thr[Ac4-beta-D-Galp-(1-->3)-Ac2-alpha-D-GalN3p]-OPfp and the application in the solid-phase peptide synthesis of multiply glycosylated mucin peptides with Tn and T antigenic structures.

Authors: H Paulsen; S Peters; T Bielfeldt; M Meldal; K Bock
Journal: Carbohydr Res Date: 1995-03-01 Impact factor: 2.104

11 in total

Review 1. Opioid glycopeptide analgesics derived from endogenous enkephalins and endorphins.

Authors: Yingxue Li; Mark R Lefever; Dhanasekaran Muthu; Jean M Bidlack; Edward J Bilsky; Robin Polt
Journal: Future Med Chem Date: 2012-02 Impact factor: 3.808

2. Parallel Glyco-SPOT Synthesis of Glycopeptide Libraries.

Authors: Akul Y Mehta; Ravi Kumar H Veeraiah; Sucharita Dutta; Christoffer K Goth; Melinda S Hanes; Chao Gao; Kathrin Stavenhagen; Robert Kardish; Yasuyuki Matsumoto; Jamie Heimburg-Molinaro; Michael Boyce; Nicola L B Pohl; Richard D Cummings
Journal: Cell Chem Biol Date: 2020-06-30 Impact factor: 8.116

3. Translation of structure-activity relationships from cyclic mixed efficacy opioid peptides to linear analogues.

Authors: Jessica P Anand; Vanessa R Porter-Barrus; Helen V Waldschmidt; Larisa Yeomans; Irina D Pogozheva; John R Traynor; Henry I Mosberg
Journal: Biopolymers Date: 2014-01 Impact factor: 2.505

4. Biodegradability and Toxicity of Cellobiosides and Melibiosides.

Authors: David E Hogan; Fei Tian; Scott W Malm; Laurel L Kegel; Lajos Z Szabo; Anoop S Hunjan; Jeanne E Pemberton; Walter T Klimecki; Robin Polt; Raina M Maier
Journal: J Surfactants Deterg Date: 2020-05-02 Impact factor: 1.902

5. Simple and Efficient Preparation of O- and S-GlcNAcylated Amino Acids through InBr₃-Catalyzed Synthesis of β- N-Acetylglycosides from Commercially Available Reagents.

Authors: Cesar A De Leon; Geoffrey Lang; Marcos I Saavedra; Matthew R Pratt
Journal: Org Lett Date: 2018-08-08 Impact factor: 6.005

Review 6. CNS active O-linked glycopeptides.

Authors: Evan M Jones; Robin Polt
Journal: Front Chem Date: 2015-06-24 Impact factor: 5.221

Review 7. Glycopeptide drugs: A pharmacological dimension between "Small Molecules" and "Biologics".

Authors: Christopher R Apostol; Meredith Hay; Robin Polt
Journal: Peptides Date: 2020-07-13 Impact factor: 3.750

8. Development of a bioavailable μ opioid receptor (MOPr) agonist, δ opioid receptor (DOPr) antagonist peptide that evokes antinociception without development of acute tolerance.

Authors: Henry I Mosberg; Larisa Yeomans; Jessica P Anand; Vanessa Porter; Katarzyna Sobczyk-Kojiro; John R Traynor; Emily M Jutkiewicz
Journal: J Med Chem Date: 2014-03-26 Impact factor: 7.446

9. Can amphipathic helices influence the CNS antinociceptive activity of glycopeptides related to β-endorphin?

Authors: Yingxue Li; Lindsay St Louis; Brian I Knapp; Dhanasekaran Muthu; Bobbi Anglin; Denise Giuvelis; Jean M Bidlack; Edward J Bilsky; Robin Polt
Journal: J Med Chem Date: 2014-03-07 Impact factor: 7.446

10. Preparation of S-glycoside surfactants and cysteine thioglycosides using minimally competent Lewis acid catalysis.

Authors: Lajos Z Szabó; Dillon J Hanrahan; Evan M Jones; Erin Martin; Jeanne E Pemberton; Robin Polt
Journal: Carbohydr Res Date: 2016-01-06 Impact factor: 2.104