This old version of Proteopedia is provided for student assignments while the new version is undergoing repairs. Content and edits done in this old version of Proteopedia after March 1, 2026 will eventually be lost when it is retired in about June of 2026.
Apply for new accounts at the new Proteopedia. Your logins will work in both the old and new versions.
1q74
From Proteopedia
| |||||||
| , resolution 1.70Å | |||||||
|---|---|---|---|---|---|---|---|
| Ligands: | , | ||||||
| Gene: | Rv1170 (Mycobacterium tuberculosis) | ||||||
| Domains: | COG2120 | ||||||
| Resources: | FirstGlance, OCA, PDBsum, RCSB | ||||||
| Coordinates: | save as pdb, mmCIF, xml | ||||||
The Crystal Structure of 1D-myo-inosityl 2-acetamido-2-deoxy-alpha-D-glucopyranoside Deacetylase (MshB)
Overview
The C2-symmetric vinyl sulfoxide, trans-2-methylene-1,3-dithiolane 1,3-dioxide, was found to react with a range of 3-oxidopyridinium betaines (bearing different substituents on nitrogen) in high yield and with total diastereoselectivity. A 2.3:1 mixture of regioisomers was formed with all of the 3-oxidopyridinium betaines but the ratio was found to change over prolonged periods of time due to reversibility of the minor regioisomer. 3-Oxidopyridinium betaines bearing methyl substituents at either the 2- or 6-position were also tested in the cycloaddition process. Improved regioselectivity (8:1) and again high diastereoselectivity were observed with the betaine having an additional substituent at the 2-position, but with betaines having a substituent in the 6-position although high regioselectivity was observed (9.9:1), the major isomer was formed with low diastereoselectivity (5.5:4.4). The origin of the regio- and diastereo-selectivity with all the betaines is discussed. Finally, the C2-symmetric vinyl sulfoxide, trans-2-methylene-1,3-dithiolane 1,3-dioxide was reacted with an oxidopyrylium betaine in moderate yield. Good regioselectivity and moderate diastereoselectivity were observed.
About this Structure
1Q74 is a Single protein structure of sequence from Mycobacterium tuberculosis. Full crystallographic information is available from OCA.
Reference
Highly diastereoselective 1,3-dipolar cycloaddition reactions of trans-2-methylene-1,3-dithiolane 1,3-dioxide with 3-oxidopyridinium and 3-oxidopyrylium betaines: a route to the tropane skeleton., Aggarwal VK, Grainger RS, Newton GK, Spargo PL, Hobson AD, Adams H, Org Biomol Chem. 2003 Jun 7;1(11):1884-93. PMID:12945769
Page seeded by OCA on Sun Mar 30 23:09:42 2008
Categories: Mycobacterium tuberculosis | Single protein | Arad, D. | Av-Gay, Y. | Cherney, M M. | Fahey, R C. | Garen, C. | James, M N. | Maynes, J T. | Newton, G. | TBSGC, TB Structural Genomics Consortium. | Protein structure initiative | Psi | Rossmann fold | Structural genomic | Tb structural genomics consortium | Tbsgc | Zinc aminohydrolase
