TMG-chitotriomycin的全合成、结构修正及构效关系研究
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摘要
2-氨基-2-脱氧糖是许多具有重要生物学意义的原核和真核生物中碳水化合物的重要组成部分,如几丁质、固氮因子和肝素等。然而,把氨基糖引入到寡糖中却是糖化学中长期存在的难题。我们发现,N-磷酸二甲酯保护的三氯乙酰亚胺酯给体与各种不同受体发生糖苷化反应,都能以高产率和良好的选择性得到β-构型糖苷化产物。而且,在不同酰氯的作用下,N-磷酸二甲酯保护基可被高效转化成氨基或其它酰基取代的氨基糖衍生物,这为合成不同酰胺交替取代的氨基寡糖提供了一种有效的方法。
2008年,日本化学家Kanzaki等报道了从链霉菌中分离鉴定出结构奇特的四糖化合物TMG-chitotriomycin,该四糖中的N-三甲基葡萄糖铵结构(TMG)前所未见,而且,该结构能引起远端糖基C2的差向异构。同时,该化合物被发现对昆虫和真菌来源的β-N-乙酰葡萄糖胺水解酶(GlcNAcase)具有较强的选择性抑制活性,是研究GlcNAcase的作用机理和发展新型抗菌药物的难得先导化合物。在本文中,我们采用汇聚式的[2+2]合成策略,使用本小组发展的以糖基邻炔基苯甲酸酯为给体、Au(Ⅰ)为促进剂的糖苷化方法,顺利构建了大立体位阻的α-(1→4)-和β-(1→4)-糖苷键,高效完成了TMG-chitotriomycin报道结构的首次全合成。然而,合成的化合物与Kanzaki等通过谱学推测的原定结构并不相符,进而我们对天然产物的结构进行了修正,把原定的α-TMG修正为β-TMG,并通过对修正结构的全合成加以了证明。接下来,我们合成了天然产物的一系列类似物,阐明了TMG-chitotriomycin抑制GlcNAcase酶的构效关系,有望发展出高效的抑制剂用于抗菌药物的研发。
另外,我们发现,在以糖基邻炔基苯甲酸酯为给体、Au(Ⅰ)为促进剂的糖苷化反应中,若把DBU和BF3·OEt2作为添加剂,则酸醇可以良好的化学选择性生成酯糖苷；而若把DTBP作为添加剂,则酸醇会选择性形成原酸酯。这为三萜皂甙中羧酸的化学选择性糖苷化反应提供了一种高效的方法。
2-Amino-2-deoxy-D-glucopyranose (D-glucosamine) is an integral component of numerous biologically important prokaryotic and eukaryotic carbohydrates, including chitin, nodulation factor and heparin. Nevertheless, introduction of the glucosamine residue into oligosaccharides has been a long-standing problem in preparative carbohydrate chemistry. We found that glycosylation of a variety of alcohols with 2-N-dimethylphosphoryl-2-deoxy-a-D-glucopyranosyl trichloroacetimidate as a glycosyl donor provided the corresponding coupled products in high yields and goodβ-selectivity. And in the presence of acyl chlorides and DMAP in pyridine, the N-dimethylphosphoryl-protection could be readily transformed into the corresponding N-acyl derivatives, this method provided an effective approach to the synthesis of glucosamine-containing oligosaccharides with alternate N-acyl substitutions.
TMG-chitotriomycin was disclosed by Kanzaki and co-workers from the culture filtrate of Streptomyces anulatus NBRC13369 in 2008, which exhibited potent and selective inhibition against theβ-N-acetylglucosaminidase (GlcNAcase) of insects and fungi and would be ideal lead compound for understanding the molecular mechanisms of GlcNAcase and the development of new antifungal agents. The proposed structrure of TMG-chitotriomycin was also intriguing in that this tetrasaccharide possesses a unique N,N,N-trimethyl-D-glucosamine (TMG) residueα-(1→4)-linked at the nonreducing end of a chitotriose; moreover, the presence of the trimethylammonium could astonishingly result in epimerization at the remote C2 of the reducing-end GlcNAc unit. In this dissertation, We developed a convergent [2+2] approach to complete the first total synthesis of the proposed structure of TMG-chitotriomycin efficiently, where the sterically demandingα-(1→4)-andβ-(1→4)-glycosidic linkages were assembled smoothly by our newly developed glycosylation protocol with glycosyl ortho-hexynylbenzoates as donors and Au(I) as the catalyst. However, the synthetic compound was apparently not identical to the natural TMG-chitotriomycin isolated by Kanzaki and co-workers, as determined by a comparison of their 1H NMR spectra. Thus we revised the structure of natural TMG-chitotriomycin. We suspected that the TMG might beβ-linked to the chitotriose in the natural product instead ofα-linked as in the previous assignment. In the event, the revised structure of TMG-chitotriomycin was validated unambiguously via the total synthesis. Then, a series of anologues of the natural product were also synthesized, which elucidated the structure-activity relationship of TMG-chitotriomycin on the selective inhibition of GlcNAcases and might be developed into efficient inhibitors for the studies of antifungal drugs.
In addition, we found that the Au(I)-catalyzed glycosylation of acid alcohols with glycosyl ortho-hexynylbenzoates in the presence of BF3·OEt2 and DBU provided the corresponding ester glycosides chemoselectively in high yield; while with DTBP as an additive instead, orthoester formation with the alcohol was effected selectively. This finding provided an effective approach to the chemoselective glycosylation of carboxylic acid in the synthesis of triterpene saponins.
2008年,日本化学家Kanzaki等报道了从链霉菌中分离鉴定出结构奇特的四糖化合物TMG-chitotriomycin,该四糖中的N-三甲基葡萄糖铵结构(TMG)前所未见,而且,该结构能引起远端糖基C2的差向异构。同时,该化合物被发现对昆虫和真菌来源的β-N-乙酰葡萄糖胺水解酶(GlcNAcase)具有较强的选择性抑制活性,是研究GlcNAcase的作用机理和发展新型抗菌药物的难得先导化合物。在本文中,我们采用汇聚式的[2+2]合成策略,使用本小组发展的以糖基邻炔基苯甲酸酯为给体、Au(Ⅰ)为促进剂的糖苷化方法,顺利构建了大立体位阻的α-(1→4)-和β-(1→4)-糖苷键,高效完成了TMG-chitotriomycin报道结构的首次全合成。然而,合成的化合物与Kanzaki等通过谱学推测的原定结构并不相符,进而我们对天然产物的结构进行了修正,把原定的α-TMG修正为β-TMG,并通过对修正结构的全合成加以了证明。接下来,我们合成了天然产物的一系列类似物,阐明了TMG-chitotriomycin抑制GlcNAcase酶的构效关系,有望发展出高效的抑制剂用于抗菌药物的研发。
另外,我们发现,在以糖基邻炔基苯甲酸酯为给体、Au(Ⅰ)为促进剂的糖苷化反应中,若把DBU和BF3·OEt2作为添加剂,则酸醇可以良好的化学选择性生成酯糖苷；而若把DTBP作为添加剂,则酸醇会选择性形成原酸酯。这为三萜皂甙中羧酸的化学选择性糖苷化反应提供了一种高效的方法。
2-Amino-2-deoxy-D-glucopyranose (D-glucosamine) is an integral component of numerous biologically important prokaryotic and eukaryotic carbohydrates, including chitin, nodulation factor and heparin. Nevertheless, introduction of the glucosamine residue into oligosaccharides has been a long-standing problem in preparative carbohydrate chemistry. We found that glycosylation of a variety of alcohols with 2-N-dimethylphosphoryl-2-deoxy-a-D-glucopyranosyl trichloroacetimidate as a glycosyl donor provided the corresponding coupled products in high yields and goodβ-selectivity. And in the presence of acyl chlorides and DMAP in pyridine, the N-dimethylphosphoryl-protection could be readily transformed into the corresponding N-acyl derivatives, this method provided an effective approach to the synthesis of glucosamine-containing oligosaccharides with alternate N-acyl substitutions.
TMG-chitotriomycin was disclosed by Kanzaki and co-workers from the culture filtrate of Streptomyces anulatus NBRC13369 in 2008, which exhibited potent and selective inhibition against theβ-N-acetylglucosaminidase (GlcNAcase) of insects and fungi and would be ideal lead compound for understanding the molecular mechanisms of GlcNAcase and the development of new antifungal agents. The proposed structrure of TMG-chitotriomycin was also intriguing in that this tetrasaccharide possesses a unique N,N,N-trimethyl-D-glucosamine (TMG) residueα-(1→4)-linked at the nonreducing end of a chitotriose; moreover, the presence of the trimethylammonium could astonishingly result in epimerization at the remote C2 of the reducing-end GlcNAc unit. In this dissertation, We developed a convergent [2+2] approach to complete the first total synthesis of the proposed structure of TMG-chitotriomycin efficiently, where the sterically demandingα-(1→4)-andβ-(1→4)-glycosidic linkages were assembled smoothly by our newly developed glycosylation protocol with glycosyl ortho-hexynylbenzoates as donors and Au(I) as the catalyst. However, the synthetic compound was apparently not identical to the natural TMG-chitotriomycin isolated by Kanzaki and co-workers, as determined by a comparison of their 1H NMR spectra. Thus we revised the structure of natural TMG-chitotriomycin. We suspected that the TMG might beβ-linked to the chitotriose in the natural product instead ofα-linked as in the previous assignment. In the event, the revised structure of TMG-chitotriomycin was validated unambiguously via the total synthesis. Then, a series of anologues of the natural product were also synthesized, which elucidated the structure-activity relationship of TMG-chitotriomycin on the selective inhibition of GlcNAcases and might be developed into efficient inhibitors for the studies of antifungal drugs.
In addition, we found that the Au(I)-catalyzed glycosylation of acid alcohols with glycosyl ortho-hexynylbenzoates in the presence of BF3·OEt2 and DBU provided the corresponding ester glycosides chemoselectively in high yield; while with DTBP as an additive instead, orthoester formation with the alcohol was effected selectively. This finding provided an effective approach to the chemoselective glycosylation of carboxylic acid in the synthesis of triterpene saponins.
引文
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