UDP-N-乙酰半乳糖胺：多肽半乳糖胺基转移酶新型抑制剂的合成
Synthesis of a new inhibitor of the UDP-GalNAc:polypeptide galactosaminyl transferase.
作者信息
Hatanaka K, Slama J T, Elbein A D
机构信息
Department of Biochemistry, University of Texas Health Science Center, San Antonio 78284.
出版信息
Biochem Biophys Res Commun. 1991 Mar 15;175(2):668-72. doi: 10.1016/0006-291x(91)91617-l.
Reaction of UDP-glucose with 1-hexadecanesulfonyl chloride (C16H33SO2Cl) in pyridine gave a new inhibitor of O-glycosylation. This reaction product was purified by TLC and shown by 1H-NMR and by chemical analysis of phosphorus to be uridine 5'-phosphoric (1-hexadecanesulfonic) anhydride. This compound was tested against the GalNAc transferase. The UMP-hexadecanesulfonic-anhydride did inhibit this enzyme with 50% inhibition requiring 160 microM. The inhibition with respect to UDP-GalNAc concentration was of the competitive type. We also synthesized the UMP-1-octanesulfonic anhydride (C8) and the UMP-butanesulfonic anhydride (C4) to see way effect fatty acid had on activity. The inhibition was in the order C16:C8:C4.
尿苷二磷酸葡萄糖（UDP-葡萄糖）与1-十六烷基磺酰氯（C16H33SO2Cl）在吡啶中反应生成了一种新的O-糖基化抑制剂。该反应产物通过薄层层析法（TLC）纯化，并经1H-核磁共振（1H-NMR）和磷的化学分析表明为尿苷5'-磷酸（1-十六烷基磺酸）酐。该化合物针对N-乙酰半乳糖胺转移酶（GalNAc转移酶）进行了测试。尿苷一磷酸-十六烷基磺酸酐确实能抑制这种酶，50%抑制率所需浓度为160微摩尔。相对于UDP-N-乙酰半乳糖胺浓度的抑制作用属于竞争性类型。我们还合成了尿苷一磷酸-1-辛基磺酸酐（C8）和尿苷一磷酸-丁基磺酸酐（C4），以观察脂肪酸链长度对活性的影响。抑制作用顺序为C16＞C8＞C4。
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