Design, synthesis, and enzymatic property of a sulfur-substituted analogue of trigalacturonic acid

doi:10.1016/j.bmcl.2005.08.019

Bioorganic & Medicinal Chemistry Letters

Volume 15, Issue 22, 15 November 2005, Pages 4932-4935

https://doi.org/10.1016/j.bmcl.2005.08.019 Get rights and content

Abstract

A sulfur-substituted analogue of trigalacturonic acid (3) was synthesized. The synthesis features the application of 3-cyano-3-(tert-butyldimethylsilyl)oxypropylthioether (CSP) as a novel protective group for thiols. This analogue was designed with the expectation that it would be a stable analogous substrate for endo-polygalacturonase isolated from Stereum purpureum based on computer modeling experiments. Surface plasmon resonance experiments revealed that 3 forms a stable complex with the target enzyme.

Graphical abstract

Section snippets

Acknowledgments

Part of these studies was financially supported by Hirosaki University as Priority Studies. We thank President Masahiko Endo of Hirosaki University for his fruitful suggestions throughout these studies.

References and notes (18)

C.D. Jensen et al.
Am. J. Cardiol.
(1997)
G. Zsivanovits et al.
Carbohydr. Res.
(2004)
T. Gidenne
Livest. Prod. Sci.
(2003)
H. Matsuda et al.
Bioorg. Med. Chem. Lett.
(2003)
H. Cao et al.
Tetrahedron Lett.
(2005)
L.J. Van den Bos et al.
Org. Lett.
(2004)
D. Magaud et al.
Tetrahedron Lett.
(1997)
R.R. Schmidt et al.
T. Shimizu et al.
Eur. J. Biochem.
(2000)

There are more references available in the full text version of this article.

Cited by (21)

Total Synthesis of the Repeating Unit of Streptococcus pneumoniae Zwitterionic Polysaccharide Sp1
2021, Journal of Organic Chemistry
Reported herein is the total synthesis of the trisaccharide repeating unit of Streptococcus pneumoniae zwitterionic polysaccharide Sp1 containing a rare sugar, 2-acetamido-4-amino-2,4,6-trideoxy-d-galactose (AAT), and three consecutive 1,2-cis-glycosidic linkages. The total synthesis was completed via highly stereoselective glycosylations and late-stage oxidation as key steps involving a longest linear sequence of 21 steps with 4.4% overall yield.
Synthesis of a trigalacturonic acid analogue mimicking the expected transition state in the glycosidases
2010, Carbohydrate Research
Citation Excerpt :
In the course of our investigations on the detailed mechanism of endo-glycosidases, we focused on endo-polygalacturonase 1 (endo-PG 1), isolated from Stereum purpureum by one of the present authors, Miyairi,5 which led to a nice single crystal of the protein that gave an X-ray diffraction structure within 0.96 Å.6,7 Recently, we have synthesized a sulfur analogue of trigalacturonic acid (1, Fig. 1) as a mimetic substrate with tolerance against the enzymatic reaction.8 It was designed to make a complex with endo-PG 1 to provide information for designing higher functional artificial mutants.
Synthesis and cytotoxicities of icogenin analogues with disaccharide residues
2009, Bioorganic and Medicinal Chemistry Letters
For further structure–activity relationships (SAR) research of furostan saponin, two icogenin analogues: (25R)-22-O-methyl-furost-5-en-3β,26-diol-3-O-α-l-rhamnopyranosyl-(1 → 2)-β-d-glucopyranoside 1 and (25R)-22-O-methyl-furost-5-en-3β,26-diol-3-O-α-l-rhamnopyranosyl-(1 → 2)-α-d-glucopyranoside 2, with valuable disaccharide moieties, were synthesized from diosgenin through eight steps. Both of the analogues behaved the similar cytotoxic activities with icogenin, towards nine types of human tumor cells herein.
α-S-GalCer: Synthesis and evaluation for iNKT cell stimulation
2008, Bioorganic and Medicinal Chemistry Letters
Synthesis of 4-thiol-furanosidic uronate: Via hydrothiolation reaction
2021, RSC Advances
Exploring Multi-Subsite Binding Pockets in Proteins: DEEP-STD NMR Fingerprinting and Molecular Dynamics Unveil a Cryptic Subsite at the GM1 Binding Pocket of Cholera Toxin B
2020, Chemistry - A European Journal

View all citing articles on Scopus

View full text

Design, synthesis, and enzymatic property of a sulfur-substituted analogue of trigalacturonic acid

Abstract

Graphical abstract

Section snippets

Acknowledgments

Am. J. Cardiol.

Carbohydr. Res.

Livest. Prod. Sci.

Bioorg. Med. Chem. Lett.

Tetrahedron Lett.

Org. Lett.

Tetrahedron Lett.

Eur. J. Biochem.