Synthesis and Evaluation of Bicyclo[3.1.0]hexane-Based UDP-Galf Analogues as Inhibitors of the Mycobacterial Galactofuranosyltransferase GlfT2
UDP-galactofuranose (UDP-Galf) is the donor substrate for both bifunctional galactofuranosyltransferases, GlfT1 and GlfT2, which are involved in the biosynthesis of mycobacterial galactan. In this paper, a group of UDP-Galf mimics were synthesized via reductive amination of a bicyclo[3.1.0]hexane-ba...
| Main Authors: | , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2016-08-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | http://www.mdpi.com/1420-3049/21/8/1053 |
| _version_ | 1828859761366401024 |
|---|---|
| author | Todd L. Lowary Jing Li |
| author_facet | Todd L. Lowary Jing Li |
| author_sort | Todd L. Lowary |
| collection | DOAJ |
| description | UDP-galactofuranose (UDP-Galf) is the donor substrate for both bifunctional galactofuranosyltransferases, GlfT1 and GlfT2, which are involved in the biosynthesis of mycobacterial galactan. In this paper, a group of UDP-Galf mimics were synthesized via reductive amination of a bicyclo[3.1.0]hexane-based amine by reacting with aromatic, linear, or uridine-containing aldehydes. These compounds were evaluated against GlfT2 using a coupled spectrophotometric assay, and were shown to be weak inhibitors of the enzyme. |
| first_indexed | 2024-12-13T02:24:51Z |
| format | Article |
| id | doaj.art-20bdf31a0cca4b839a9c8d7eea1225a0 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-13T02:24:51Z |
| publishDate | 2016-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-20bdf31a0cca4b839a9c8d7eea1225a02022-12-22T00:02:40ZengMDPI AGMolecules1420-30492016-08-01218105310.3390/molecules21081053molecules21081053Synthesis and Evaluation of Bicyclo[3.1.0]hexane-Based UDP-Galf Analogues as Inhibitors of the Mycobacterial Galactofuranosyltransferase GlfT2Todd L. Lowary0Jing Li1Department of Chemistry and Alberta Glycomics Centre, University of Alberta, 11227 Saskatchewan Drive, Edmonton, AB T6G2G2, CanadaCollege of Life Science and Technology, Heilongjiang Bayi Agricultural University, Daqing 163319, Heilongjiang Province, ChinaUDP-galactofuranose (UDP-Galf) is the donor substrate for both bifunctional galactofuranosyltransferases, GlfT1 and GlfT2, which are involved in the biosynthesis of mycobacterial galactan. In this paper, a group of UDP-Galf mimics were synthesized via reductive amination of a bicyclo[3.1.0]hexane-based amine by reacting with aromatic, linear, or uridine-containing aldehydes. These compounds were evaluated against GlfT2 using a coupled spectrophotometric assay, and were shown to be weak inhibitors of the enzyme.http://www.mdpi.com/1420-3049/21/8/1053mycobacteriatuberculosisgalactofuranosyltransferasesUDP-Galfinhibitorsreductive amination |
| spellingShingle | Todd L. Lowary Jing Li Synthesis and Evaluation of Bicyclo[3.1.0]hexane-Based UDP-Galf Analogues as Inhibitors of the Mycobacterial Galactofuranosyltransferase GlfT2 Molecules mycobacteria tuberculosis galactofuranosyltransferases UDP-Galf inhibitors reductive amination |
| title | Synthesis and Evaluation of Bicyclo[3.1.0]hexane-Based UDP-Galf Analogues as Inhibitors of the Mycobacterial Galactofuranosyltransferase GlfT2 |
| title_full | Synthesis and Evaluation of Bicyclo[3.1.0]hexane-Based UDP-Galf Analogues as Inhibitors of the Mycobacterial Galactofuranosyltransferase GlfT2 |
| title_fullStr | Synthesis and Evaluation of Bicyclo[3.1.0]hexane-Based UDP-Galf Analogues as Inhibitors of the Mycobacterial Galactofuranosyltransferase GlfT2 |
| title_full_unstemmed | Synthesis and Evaluation of Bicyclo[3.1.0]hexane-Based UDP-Galf Analogues as Inhibitors of the Mycobacterial Galactofuranosyltransferase GlfT2 |
| title_short | Synthesis and Evaluation of Bicyclo[3.1.0]hexane-Based UDP-Galf Analogues as Inhibitors of the Mycobacterial Galactofuranosyltransferase GlfT2 |
| title_sort | synthesis and evaluation of bicyclo 3 1 0 hexane based udp galf analogues as inhibitors of the mycobacterial galactofuranosyltransferase glft2 |
| topic | mycobacteria tuberculosis galactofuranosyltransferases UDP-Galf inhibitors reductive amination |
| url | http://www.mdpi.com/1420-3049/21/8/1053 |
| work_keys_str_mv | AT toddllowary synthesisandevaluationofbicyclo310hexanebasedudpgalfanaloguesasinhibitorsofthemycobacterialgalactofuranosyltransferaseglft2 AT jingli synthesisandevaluationofbicyclo310hexanebasedudpgalfanaloguesasinhibitorsofthemycobacterialgalactofuranosyltransferaseglft2 |