Synthesis of CH2-linked α-galactosylceramide and its glucose analogues through glycosyl radical-mediated direct C-glycosylation

2020 ◽  
Vol 56 (34) ◽  
pp. 4712-4715 ◽  
Author(s):  
Yu Hidaka ◽  
Noriaki Kiya ◽  
Makoto Yoritate ◽  
Kazuteru Usui ◽  
Go Hirai
Keyword(s):  
Conformationally Constrained ◽  
Glucose Analogues

Direct C-glycosylation of a conformationally constrained and stable C1-sp3 hybridized carbohydrate donor with a carefully designed sphingosine unit afforded the CH2-linked analogue of antitumor-active KRN7000 and its glucose congener.

Conformationally Constrained Peptide Drugs Targeted at the Blood-Brain Barrier

1995 ◽  
Author(s):  
Thomas P. Davis ◽  
Thomas J. Abbruscato ◽  
Elizabeth Brownson ◽  
Victor J. Hruby
Keyword(s):  
Blood Brain Barrier ◽  
Brain Barrier ◽  
Peptide Drugs ◽  
Conformationally Constrained ◽  
Blood Brain

A Fast and Sensitive Method Combining Reversed-Phase Chromatography with High Resolution Mass Spectrometry to Quantify 2-Fluoro-2-Deoxyglucose and Its Phosphorylated Metabolite for Determining Glucose Uptake

2019 ◽  
Author(s):  
Ashley Williams ◽  
Deborah Muoio ◽  
Guofang Zhang
Keyword(s):  
Glucose Uptake ◽  
Biological Samples ◽  
High Resolution Mass Spectrometry ◽  
Reversed Phase ◽  
Sodium Adduct ◽  
Negative Mode ◽  
Glucose Analogues ◽  
Positive Mode ◽  
Q Exactive ◽  
Glucose Analogue

Quantative measurements of the glucose analogue, 2-deoxyglucose (2DG), and its phosphorylated metabolite (2-deoxyglucose-6-phosphate (2DG-6-P)) are critical for the measurement of glucose uptake. While the field has long identified the need for sensitive and reliable assays that deploy non-radiolabled glucose analogues to assess glucose uptake, no analytical MS-based methods exist to detect trace amounts in complex biological samples. In the present work, we show that 2DG is poorly suited for MS-based methods due to interfering metabolites. We therefore developed and validated an alternative C18-based LC-Q-Exactive-Orbitrap-MS method using 2-fluoro-2-deoxyglucose (2FDG) to quantify both 2FDG and 2FDG-6-P by measuring the sodium adduct of 2FDG in the positive mode and deprotonation of 2FDG-6-P in the negative mode. The low detection limit of this method can reach 81.4 and 48.8 fmol for both 2FDG and 2FDG-6-P, respectively. The newly developed method was fully validated via calibration curves in the presence and absence of biological matrix. The present work is the first successful LC-MS method that can quantify trace amounts of a nonradiolabeled glucose analogue and its phosphorylated metabolite and is a promising analytical method to determine glucose uptake in biological samples.

Pyrrolidine nucleotides conformationally constrained via hydrogen bonding

2014 ◽  
Author(s):  
Radek Pohl ◽  
Lenka Poštová Slavětínská ◽  
Dominik Rejman
Keyword(s):  
Hydrogen Bonding ◽  
Conformationally Constrained

scholarly journals Small and Simple, yet Sturdy: Conformationally Constrained Peptides with Remarkable Properties

2021 ◽  
Vol 22 (4) ◽  
pp. 1611
Author(s):  
Krištof Bozovičar ◽  
Tomaž Bratkovič
Keyword(s):  
Chemical Space ◽  
Structure Optimization ◽  
Peptide Chain ◽  
Conformationally Constrained ◽  
Drug Candidates ◽  
Conformational Constraints ◽  
Macrocyclic Peptides ◽  
Constrained Peptides ◽  
Sheer Size

The sheer size and vast chemical space (i.e., diverse repertoire and spatial distribution of functional groups) underlie peptides’ ability to engage in specific interactions with targets of various structures. However, the inherent flexibility of the peptide chain negatively affects binding affinity and metabolic stability, thereby severely limiting the use of peptides as medicines. Imposing conformational constraints to the peptide chain offers to solve these problems but typically requires laborious structure optimization. Alternatively, libraries of constrained peptides with randomized modules can be screened for specific functions. Here, we present the properties of conformationally constrained peptides and review rigidification chemistries/strategies, as well as synthetic and enzymatic methods of producing macrocyclic peptides. Furthermore, we discuss the in vitro molecular evolution methods for the development of constrained peptides with pre-defined functions. Finally, we briefly present applications of selected constrained peptides to illustrate their exceptional properties as drug candidates, molecular recognition probes, and minimalist catalysts.

An Enantiodefined Conformationally Constrained Fatty Acid Mimetic and Potent Inhibitor of ToxT

2021 ◽  
Author(s):  
Lauren E. Markham ◽  
Jessica D. Tolbert ◽  
F. Jon Kull ◽  
Charles R. Midgett ◽  
Glenn C. Micalizio
Keyword(s):  
Fatty Acid ◽  
Potent Inhibitor ◽  
Conformationally Constrained

Insights into the Distance Dependence of Electron Transfer through Conformationally Constrained Peptides

2020 ◽  
Vol 7 (5) ◽  
pp. 1225-1237
Author(s):  
Claudio Zuliani ◽  
Fernando Formaggio ◽  
Laura Scipionato ◽  
Claudio Toniolo ◽  
Sabrina Antonello ◽  
...  
Keyword(s):  
Electron Transfer ◽  
Conformationally Constrained ◽  
Distance Dependence ◽  
Constrained Peptides

Synthesis of Conformationally Constrained Glutamic Acid Homologues and Investigation of Their Pharmacological Profiles

ChemMedChem ◽  
2007 ◽  
Vol 2 (11) ◽  
pp. 1639-1647 ◽  
Author(s):  
Paola Conti ◽  
Andrea Pinto ◽  
Lucia Tamborini ◽  
Giovanni Grazioso ◽  
Giovambattista De Sarro ◽  
...  
Keyword(s):  
Glutamic Acid ◽  
Conformationally Constrained ◽  
Pharmacological Profiles

Conformationally constrained precursors to retinoic acid analogs which stabilize the 9Z-configuration

1995 ◽  
Vol 5 (9) ◽  
pp. 953-958 ◽  
Author(s):  
Cynthia Y. Robinson ◽  
D.Vincent Waterhous ◽  
Donald D. Muccio ◽  
Wayne J. Brouillette
Keyword(s):  
Retinoic Acid ◽  
Conformationally Constrained
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