O-Benzoylation as a derivatization procedure for analysis of 1-monomycoloylglycerol by mass spectrometry

✍ Scribed by Thuioshi Ioneda

• Book ID: 103040855
• Publisher: Elsevier Science
• Year: 1990
• Tongue: English
• Weight: 283 KB
• Volume: 53
• Category: Article
• ISSN: 0009-3084
• DOI: 10.1016/0009-3084(90)90033-n

✦ Synopsis

Benzoyl groups were attached to hydroxyl groups of monomycoloylglycerol isolated from Rhodococcus rhodochrous and R. lent~fragmentus. The resulting benzoyl monomycoloylglycerol displayed a characteristic infrared spectrum in the fingerprint region with two strong absorptions at 1110 cm -~ and 1267 cm -~, respectively. In addition, bands characteristic of the O-perbenzoyl derivative appeared at 1603 cm -~ and 1693 cm -l. Moreover, the mass spectrum of O-perbenzoylmonomycoloyglycerol using electron impact spectroscopy showed the following fragmentation peaks: (a) a peak representing the glycerol backbone; (b) a peak related to the glycerol backbone linked to a segment of the mycolic acid corresponding to the a-unit, which revealed the length of the side chain of that unit, finally (c) a series of peaks corresponding to the whole carbon chain length of the mycolic acid moiety, i.e., acylium ion minus benzoic acid.