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Selective derivatization of nucleotide diphosphate (NDP)-4-keto sugars for electrospray ionization-mass spectrometry (ESI-MS).

Journal of chromatography. B, Analytical technologies in the biomedical and life sciences (2012-03-31)
Yun-Gon Kim, Hyung-Yeon Park, Dongwon Yoo, Changmin Sung, Eunjung Song, Jae-Hun Lee, Yun-Hui Choi, Yong-Hyun Kim, Chang-Soo Lee, Kyungmoon Park, Byung-Gee Kim, Yung-Hun Yang
ABSTRACT

Nucleotide diphosphate (NDP) sugars are widely present in antibiotics and glycoconjugates, such as protein- and lipid-linked oligosaccharides, where they act as substrates for glycosyltransferase in eukaryotes and prokaryotes. Among NDP sugars, NDP-4-keto sugars are key intermediates in the synthesis of structurally diverse NDP sugars with different functional groups. However, the structural identification of the NDP-4-keto sugars via mass spectrometry (electrospray ionization-mass spectrometry (ESI-MS)) continues to be a challenge because of the carbonyl group in these sugars interferes with ionization process. In this study, we evaluated various hydroxylamine compounds for the derivatization of NDP-4-keto sugars, so that the detection of the sugars by ESI-MS is more efficient. As a result, O-(2,3,4,5,6-pentafluorobenzyl)hydroxylamine was found to be the most effective tagging molecule for the detection of NDP-4-keto sugars without being interfered by original MS. This method can be used for identifying NDP-4-keto sugars such as thymidine diphosphate (TDP)-, adenosine diphosphate (ADP)-, uridine diphosphate (UDP)-, and cytosine diphosphate (CDP)-4-keto sugars as well as new NDP-4-keto-dehydratases.

MATERIALS
Product Number
Brand
Product Description

Supelco
O-(2,3,4,5,6-Pentafluorobenzyl)hydroxylamine hydrochloride, for GC derivatization, LiChropur, ≥99.0% (AT)
Sigma-Aldrich
O-(2,3,4,5,6-Pentafluorobenzyl)hydroxylamine hydrochloride, ≥98%