Synthesis of the glycopeptide - O-(3,4-di-O-methyl-2-O-[3,4-di-O-methyl-α-L-rhamnopyranosyl]-α-L-rhamnopyranosyl)-L-alanilol: An unusual part structure in the glycopeptidolipid of Mycobacterium fortuitum

doi:10.1016/S0040-4020(01)88483-0

Tetrahedron

Volume 48, Issue 19, 1992, Pages 4039-4044

https://doi.org/10.1016/S0040-4020(01)88483-0 Get rights and content

Abstract

The stereoselective synthesis of the title compound, an unusual variant in the structure of glycopeptidolipid of $M$ . $fortuitum$ , by involving glycosyltrichloroacetimidate methodology has been described.

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Cited by (12)

(−)-Lyngbyaloside B, a Marine Macrolide Glycoside: Total Synthesis and Stereochemical Revision
2016, Strategies and Tactics in Organic Synthesis
Citation Excerpt :
Our synthesis plan toward 5 is summarized in Scheme 1. Stereoselective glycosylation by using the trichloroacetimidate 630 under Schmidt conditions31,32 would be suitable for introducing the 3,4-di-O-methyl-α-l-rhamnopyranoside moiety. The conjugated diene side chain would be constructed in a stereoselective fashion by a sequence of a Takai iodoolefination33 and a Stille reaction.34
This account describes our endeavors on the total synthesis and structure elucidation of a marine macrolide glycoside, (−)-lyngbyaloside B. This natural product was isolated as a moderately cytotoxic constituent from the Palauan cyanobacterium Lyngbya sp. Our investigation started with the total synthesis of a nonnatural analog, (−)-13-demethyllyngbyaloside B, which was completed by exploiting an esterification/ring-closing metathesis strategy for the construction of the macrocyclic framework. Our efforts toward (−)-lyngbyaloside B were frustrated by the difficulties associated with the construction of the macrocycle involving an acylated tertiary alcohol. Eventually, the first total synthesis of the proposed structure of (−)-lyngbyaloside B was completed via an acyl ketene macrocyclization to forge the macrocyclic backbone. Because the proposed structure turned out to be erroneously assigned, we deduced the correct structure of (−)-lyngbyaloside B on the basis of the NMR data of the authentic material and molecular modeling. Ultimately, our revised structure was unambiguously verified through total synthesis.
The Variable Surface Glycolipids of Mycobacteria: Structures, Synthesis of Epitopes, And Biological Properties
1995, Advances in Carbohydrate Chemistry and Biochemistry
This chapter describes the structure and synthesis of epitopes and elaborates the biological properties of the variable surface glycolipids of mycobacteria. It also presents the detailed procedures for the isolation and purification of the species-specific glycolipids of mycobacteria. Large quantities of acylglycerols and phosphoglycerides are present, and it is often impossible to isolate specific glycopeptidolipids (GPLs) in preparative amounts directly from these extracts. The relative alkaline stability of the GPLs may be exploited under conditions that result in the saponification of acyl esters when the crude lipid extract, in 2:1 chloroform–methanol, is treated with an equal volume of 0.2 M sodium hydroxide. The direct compositional analysis of glycolipids from mycobacteria remains the simplest and most necessary first step, in the light of the widespread occurrence of endogenously methylated glycose residues. Hydrolysis of the glycolipid, followed by the identification by gas-chromatographic mass spectroscopy (GC-MS) using capillary columns of the derived alditol acetates, is most appropriate because this method allows for the location of the methyl ether substituents when these are present. The anomeric and ring configurations of glycosyl residues are also elaborated in the chapter.
Synthesis of 2-amino-3-hydroxyacetophenone-0β-D-glucopyranoside : a fluorescent compound from insoluble protein fraction of aging human lens
1994, Bioorganic and Medicinal Chemistry Letters
Synthesis of the terminal trisaccharide unit of the lipo-oligosaccharide from Mycobacterium linda
1993, Carbohydrate Research
Synthesis of the complete glycotetrapeptide core of structurally variant Mycobacterium fortuitum glycopeptidolipid
1993, Bioorganic and Medicinal Chemistry Letters
Organic Synthesis with Carbohydrates
2008, Organic Synthesis with Carbohydrates

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Tetrahedron

Synthesis of the glycopeptide - O-(3,4-di-O-methyl-2-O-[3,4-di-O-methyl-α-L-rhamnopyranosyl]-α-L-rhamnopyranosyl)-L-alanilol: An unusual part structure in the glycopeptidolipid of Mycobacterium fortuitum

Abstract

Microbiol

Tetrahedron Lett.

J. Ann. Microbiol

Biochem., Biophy., Acta.

Carbohydr. Res.

Adv. Carbohydr. Chem. Biochem.

(−)-Lyngbyaloside B, a Marine Macrolide Glycoside: Total Synthesis and Stereochemical Revision

The Variable Surface Glycolipids of Mycobacteria: Structures, Synthesis of Epitopes, And Biological Properties

Synthesis of 2-amino-3-hydroxyacetophenone-0β-D-glucopyranoside : a fluorescent compound from insoluble protein fraction of aging human lens

Synthesis of the terminal trisaccharide unit of the lipo-oligosaccharide from Mycobacterium linda

Synthesis of the complete glycotetrapeptide core of structurally variant Mycobacterium fortuitum glycopeptidolipid

Organic Synthesis with Carbohydrates

Synthesis of the glycopeptide - O-(3,4-di-O-methyl-2-O-[3,4-di-O-methyl-α-L-rhamnopyranosyl]-α-L-rhamnopyranosyl)-L-alanilol: An unusual part structure in the glycopeptidolipid of $Mycobacterium$ $fortuitum$