Automated glycan assembly using the Glyconeer 2.1 synthesizer

Reliable and rapid access to defined biopolymers by automated DNA and peptide synthesis has fundamentally altered biological research and medical practice. Similarly, the procurement of defined glycans is key to establishing structure–activity relationships and thereby progress in the glycosciences. Here, we describe the rapid assembly of oligosaccharides using the commercially available Glyconeer 2.1 automated glycan synthesizer, monosaccharide building blocks, and a linker-functionalized polystyrene solid support. Purification and quality-control protocols for the oligosaccharide products have been standardized. Synthetic glycans prepared in this way are useful reagents as the basis for glycan arrays, diagnostics, and carbohydrate-based vaccines.

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An Entirely Solid Phase Peptide Synthesis-Based Strategy for Synthesis of Gelatinase Biosynthesis-Activating Pheromone (GBAP) Analogue Libraries: Investigating the Structure–Activity Relationships of the Enterococcus faecalis Quorum Sensing Signal

Organic Letters ◽

10.1021/acs.orglett.7b01444 ◽

2017 ◽

Vol 19 (12) ◽

pp. 3295-3298 ◽

Cited By ~ 11

Author(s):

Dominic N. McBrayer ◽

Brooke K. Gantman ◽

Crissey D. Cameron ◽

Yftah Tal-Gan

Keyword(s):

Quorum Sensing ◽

Enterococcus Faecalis ◽

Peptide Synthesis ◽

Solid Phase ◽

Solid Phase Peptide Synthesis ◽

Structure Activity Relationships ◽

Structure Activity

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Analogs of the CLV3 Peptide: Synthesis and Structure-Activity Relationships Focused on Proline Residues

Plant and Cell Physiology ◽

10.1093/pcp/pcq146 ◽

2010 ◽

Vol 52 (1) ◽

pp. 30-36 ◽

Cited By ~ 17

Author(s):

T. Kondo ◽

K. Yokomine ◽

A. Nakagawa ◽

Y. Sakagami

Keyword(s):

Peptide Synthesis ◽

Structure Activity Relationships ◽

Structure Activity

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Convergent Synthesis of Thioether Containing Peptides

Molecules ◽

10.3390/molecules25010218 ◽

2020 ◽

Vol 25 (1) ◽

pp. 218

Author(s):

Spyridon Mourtas ◽

Christina Katakalou ◽

Dimitrios Gatos ◽

Kleomenis Barlos

Keyword(s):

Carboxylic Acids ◽

Peptide Synthesis ◽

Solid Phase ◽

Solid Phase Peptide Synthesis ◽

Building Blocks ◽

Solid Support ◽

Convergent Synthesis ◽

Fmoc Group ◽

Synthetic Routes ◽

Peptide Elongation

Thioether containing peptides were obtained following three synthetic routes. In route A, halo acids esterified on 2-chlorotrityl(Cltr) resin were reacted with N-fluorenylmethoxycarbonyl (Fmoc) aminothiols. These were either cleaved from the resin to the corresponding (Fmoc-aminothiol)carboxylic acids, which were used as key building blocks in solid phase peptide synthesis (SPPS), or the N-Fmoc group was deprotected and peptide chains were elongated by standard SPPS. The obtained N-Fmoc protected thioether containing peptides were then condensed either in solution, or on solid support, with the appropriate amino components of peptides. In route B, the thioether containing peptides were obtained by the reaction of N-Fmoc aminothiols with bromoacetylated peptides, which were synthesized on Cltr-resin, followed by removal of the N-Fmoc group and subsequent peptide elongation by standard SPPS. In route C, the thioether containing peptides were obtained by the condensation of a haloacylated peptide synthesized on Cltr-resin and a thiol-peptide synthesized either on 4-methoxytrityl(Mmt) or trityl(Trt) resin.

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The solid phase supported peptide synthesis of analogues of the lantibiotic lactocin S

MedChemComm ◽

10.1039/c2md20014g ◽

2012 ◽

Vol 3 (8) ◽

pp. 971-975 ◽

Cited By ~ 10

Author(s):

Shaun M. K. McKinnie ◽

Avena C. Ross ◽

Michael J. Little ◽

John C. Vederas

Keyword(s):

Oxidative Stability ◽

Peptide Synthesis ◽

Solid Phase ◽

Atmospheric Oxygen ◽

Solid Phase Peptide Synthesis ◽

Lactobacillus Sakei ◽

Structure Activity Relationships ◽

Structure Activity

Four analogues of lactocin S, an antimicrobial lantibiotic peptide produced by Lactobacillus sakei L45, have been generated using solid phase peptide synthesis. These compounds show enhanced oxidative stability to atmospheric oxygen and provide information on structure–activity relationships.

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Expansion of the structure–activity relationships of BACE1 inhibitors by harnessing diverse building blocks prepared using a unified synthetic approach

MedChemComm ◽

10.1039/c9md00085b ◽

2019 ◽

Vol 10 (4) ◽

pp. 616-620

Author(s):

Joan Mayol-Llinàs ◽

Shiao Chow ◽

Adam Nelson

Keyword(s):

Amyloid Precursor Protein ◽

Structural Diversity ◽

Building Blocks ◽

Precursor Protein ◽

Synthetic Approach ◽

Structure Activity Relationships ◽

Structure Activity

The structural diversity of β-site amyloid precursor protein cleaving enzyme 1 (BACE1) inhibitors was expanded by harnessing diverse building blocks that had been prepared via a unified lead-oriented synthetic approach.

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