The Selective Activation of Telluro- over Seleno-β-D-glucopyranosides as Glycosyl Donors: a Reactivity Scale for Various Telluro, Seleno and Thio Sugars

1997 ◽  
Vol 50 (3) ◽  
pp. 237 ◽  
Author(s):  
Robert V. Stick ◽  
D. Matthew G. Tilbrook ◽  
Spencer J. Williams
Keyword(s):  
Trifluoromethanesulfonic Acid ◽  
Selective Activation ◽  
The One ◽  
Glycosyl Donors

Phenyl tetra-O-benzoyl-1-telluro-β-D-glucopyranoside, when treated with 1,2:3,4-di-O-isopropylidene-α-D-galactose in the presence of N-iodosuccinimide and trifluoromethanesulfonic acid, immediately forms the expected β-disaccharide derivative. A subsequent experiment involving both a telluroglycoside and a selenoglycoside as donors with the one alcohol acceptor showed complete preference for the telluroglycoside. This result has led to an extension of the investigation to establish a ‘reactivity scale’ for various telluro, seleno and thio sugars.

scholarly journals General synthetic strategy for regioselective ultrafast formation of disulfide bonds in peptides and proteins

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Shay Laps ◽  
Fatima Atamleh ◽  
Guy Kamnesky ◽  
Hao Sun ◽  
Ashraf Brik
Keyword(s):  
Drug Discovery ◽  
Disulfide Bonds ◽  
Unsolved Problem ◽  
De Novo ◽  
Therapeutic Potential ◽  
Selective Activation ◽  
One Pot ◽  
Synthetic Strategy ◽  
The One ◽  
Game Changer

AbstractDespite six decades of efforts to synthesize peptides and proteins bearing multiple disulfide bonds, this synthetic challenge remains an unsolved problem in most targets (e.g., knotted mini proteins). Here we show a de novo general synthetic strategy for the ultrafast, high-yielding formation of two and three disulfide bonds in peptides and proteins. We develop an approach based on the combination of a small molecule, ultraviolet-light, and palladium for chemo- and regio-selective activation of cysteine, which enables the one-pot formation of multiple disulfide bonds in various peptides and proteins. We prepare bioactive targets of high therapeutic potential, including conotoxin, RANTES, EETI-II, and plectasin peptides and the linaclotide drug. We anticipate that this strategy will be a game-changer in preparing millions of inaccessible targets for drug discovery.

scholarly journals De Novo Synthetic Design for Ultrafast Formation of Disulfide Bonds in Peptides and Proteins .pdf

2020 ◽  
Author(s):  
Shay Laps ◽  
Fatima Atamleh ◽  
Guy Kamnesky ◽  
Hao Sun ◽  
ashraf brik
Keyword(s):  
Disulfide Bonds ◽  
Unsolved Problem ◽  
De Novo ◽  
Therapeutic Potential ◽  
Uv Light ◽  
Selective Activation ◽  
One Pot ◽  
Synthetic Strategy ◽  
The One ◽  
Game Changer

<p><b>Despite six decades of efforts to synthesize peptides and proteins bearing multiple disulfide bonds, this synthetic challenge remains an unsolved problem in most targets (e.g. knotted mini proteins). Here we show a de novo general synthetic strategy for the ultrafast, high-yielding formation of two and three disulfide bonds in peptides and proteins. We developed an approach based on the combination of a small molecule, UV-light, and palladium for chemo- and regio-selective activation of Cys, which enables the one-pot formation of multiple disulfide bonds in various peptides and proteins. We prepared bioactive targets of high therapeutic potential, including conotoxin, RANTES, EETI-II, and plectasin peptides and the linaclotide drug. We anticipate that this strategy will be a game-changer in preparing millions of inaccessible targets for drug discovery.</b><br></p>

A strategy for the one-pot synthesis of sialylated oligosaccharides

2002 ◽  
Vol 80 (8) ◽  
pp. 1051-1054 ◽  
Author(s):  
Zhiyuan Zhang ◽  
Kenichi Niikura ◽  
Xue-Fei Huang ◽  
Chi-Huey Wong
Keyword(s):  
Sialic Acid ◽  
One Pot ◽  
One Pot Synthesis ◽  
New Strategy ◽  
The One ◽  
Glycosyl Donors

A new strategy has been developed for the synthesis of branched sialylated oligosaccharides using one-pot technology. Sialyl donors are in general too weak in reactivity to be used as the first glycosyl donors in the one-pot synthesis. When sialic acid is linked to a different sugar such as galactose, the reactivity is, however, significantly enhanced and can be tuned to enable the one-pot synthesis. A combination of NIS–TfOH–AgOTf was used for activation of the thioglycosides to improve the glycosylation yield when a hindered acceptor was used, as illustrated in the one-pot assembly of sialylated hexasaccharide.Key words: one-pot synthesis, sialyl oligosaccharides, new activation.

scholarly journals De Novo Synthetic Design for Ultrafast Formation of Disulfide Bonds in Peptides and Proteins .pdf

2020 ◽  
Author(s):  
Shay Laps ◽  
Fatima Atamleh ◽  
Guy Kamnesky ◽  
Hao Sun ◽  
ashraf brik
Keyword(s):  
Disulfide Bonds ◽  
Unsolved Problem ◽  
De Novo ◽  
Therapeutic Potential ◽  
Uv Light ◽  
Selective Activation ◽  
One Pot ◽  
Synthetic Strategy ◽  
The One ◽  
Game Changer

<p><b>Despite six decades of efforts to synthesize peptides and proteins bearing multiple disulfide bonds, this synthetic challenge remains an unsolved problem in most targets (e.g. knotted mini proteins). Here we show a de novo general synthetic strategy for the ultrafast, high-yielding formation of two and three disulfide bonds in peptides and proteins. We developed an approach based on the combination of a small molecule, UV-light, and palladium for chemo- and regio-selective activation of Cys, which enables the one-pot formation of multiple disulfide bonds in various peptides and proteins. We prepared bioactive targets of high therapeutic potential, including conotoxin, RANTES, EETI-II, and plectasin peptides and the linaclotide drug. We anticipate that this strategy will be a game-changer in preparing millions of inaccessible targets for drug discovery.</b><br></p>

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