唾液酸的研究。XV: 3-脱氧-d -甘油-d -半乳糖-2-nonulopyranosonic acid (KDN) α-和β- o-糖苷的合成

IF 1.5 4区医学 Q4 CHEMISTRY, MEDICINAL

Chemical & pharmaceutical bulletin Pub Date : 1988-12-25 DOI:10.1248/CPB.39.3140

Mitsunobu Nakamura, K. Furuhata, H. Ogura

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引用次数: 29

摘要

采用碱催化缩合法制备了3-脱氧- d -甘油- d -半乳糖-2-非磺酰基丙酮酸(KDN)。此外，以(4,5,7,8,9 -penta- o- acety1-3- de氧-d -glycero-a- d -半乳糖-2-nonulopyranosyl bromid)-酸苄酯为糖基供体，在koenigs - knorr -类反应条件下合成了(3-脱氧-d -glycero-β- d -半乳糖-2- nonulopyranosyd)- α和(2-(5-胆甾-3- β-yloxy)-3-脱氧-d -乙二醇-α和β- d -半乳糖-2-nonulopyranosyl)-酸苄酯和(2-(5-胆甾-3- β-yloxy)钠。通过质子核磁共振和圆二色光谱分析对糖基化产物的结构和立体化学进行了表征。

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Studies on sialic acids. XV: Synthesis of α- and β-O-glycosides of 3-deoxy-D-glycero-D-galacto-2-nonulopyranosonic acid (KDN)

3-Deoxy-D-glycero-D-galacto-2-nonulopyranosonic acid (KDN) was synthesized by basecatalyzed condensation in good yield. Furthermore, benzyl (methyl 3-deoxy-D-glycero-a-D-galacto-2-nonulopyranosid) onate and sodium 2-(5-cholesten-3β-yloxy)-3-deoxy-D-eycero-α-and β-D-galacto-2-nonulopyranosonate were synthesized under Koenigs-Knorr-like reaction conditions, using benzyl (4, 5, 7, 8, 9-penta-O-acety1-3-deoxy-D-glycero-β-D-galacto-2-nonulopyranosyl bromid)-onate as a glycosyl donor. The structure and the stereochemistry of glycosylation products were determined by proton nuclear magnetic resonance and circular dichroism spectral analysis.

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来源期刊

Chemical & pharmaceutical bulletin 医学-化学综合

CiteScore

3.20

自引率

5.90%

发文量

132

审稿时长

1.7 months

期刊介绍： The CPB covers various chemical topics in the pharmaceutical and health sciences fields dealing with biologically active compounds, natural products, and medicines, while BPB deals with a wide range of biological topics in the pharmaceutical and health sciences fields including scientific research from basic to clinical studies. For details of their respective scopes, please refer to the submission topic categories below. Topics: Organic chemistry In silico science Inorganic chemistry Pharmacognosy Health statistics Forensic science Biochemistry Pharmacology Pharmaceutical care and science Medicinal chemistry Analytical chemistry Physical pharmacy Natural product chemistry Toxicology Environmental science Molecular and cellular biology Biopharmacy and pharmacokinetics Pharmaceutical education Chemical biology Physical chemistry Pharmaceutical engineering Epidemiology Hygiene Regulatory science Immunology and microbiology Clinical pharmacy Miscellaneous.