Mycoplasma pneumoniae expresses β-glycolipids (β-GGLs) in cytoplasmic membranes, which possess a unique β(1 → 6)-linked disaccharide epitope, which has high potential in biochemical and medicinal applications. In the present study, a series of β-GGLs homologues with different acyl chains (C12, C14, C16, and C18) were prepared from a common precursor. An ELISA assay using an anti-(β-GGLs) monoclonal antibody indicated that the synthetic homologues with long acyl chains had greater diagnostic potential in the order C18 > C16 > C14 > C12. Toward a simultaneous detection of natural glycolipids by mass spectrometry (MS), a deuterium-labeled C16 homologue (β-GGL-C16-d₃) was prepared and applied as an internal standard for a high-resolution electrospray ionization MS (ESI-MS) analysis. The ESI-MS analysis was used to identify and quantify acyl homologues (C16/C16, C16/C18, and C18/C18) of β-GGL-C16 in cultured M. pneumoniae. A β-GGLs homologue with a 1,2-diacetyl group (C2) was also prepared as a “water soluble” glycolipid homologue and characterized by ¹H NMR spectroscopy. We envisage that each of these chemosynthetic homologues will provide promising approaches to solve medical and biological problems associated with mycoplasma infectious diseases (MIDs).

肺炎支原体在细胞质膜中表达β-糖脂（β-GGLs），其具有独特的与β（1→6）连接的二糖表位，在生化和医学应用中具有很高的潜力。在本研究中，从共同的前体制备了一系列具有不同酰基链（C12，C14，C16和C18）的β-GGLs同源物。使用抗-（β-GGLs）单克隆抗体的ELISA分析表明，具有长酰基链的合成同源物具有更大的诊断潜力，顺序为C18> C16> C14> C12。为了通过质谱（MS）同时检测天然的糖脂，一种氘标记的C16同源物（β-GGL-C16- d ₃制备），并将其用作高分辨率电喷雾电离MS（ESI-MS）分析的内标。ESI-MS分析用于鉴定和定量培养的肺炎支原体中β-GGL-C16的酰基同系物（C16 / C16，C16 / C18和C18 / C18）。还制备了具有1,2-二乙酰基（C2）的β-GGLs同源物，作为“水溶性”糖脂同源物，并通过¹ H NMR光谱进行了表征。我们设想，每个这些化学合成同源物将提供有希望的方法来解决与支原体感染性疾病（MID）相关的医学和生物学问题。