Synthesis of an artificial antigen that corresponds to a disaccharide repeating unit of the capsular polysaccharide of Haemophilus influenzae type d. A facile synthesis of methyl 2-acetamido-2-deoxy-β- d -mannopyranoside

Classon, Björn; Garegg, Per J.; Oscarson, Stefan; Tidén, Anna-Karin

doi:10.1016/0008-6215(92)84161-k

Cited by 36 publications

(15 citation statements)

References 18 publications

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“…A challenging aspect of the preparation of target compound 2 is the installment of a β‐mannosamine moiety 27. A strategy was adopted in which a β‐glucoside is initially installed by using a glucosyl donor that has a participating ester‐protecting group at C‐2 to control β‐anomeric selectivity 32. Next, the C‐2 protecting group can be removed and the resulting hydroxyl triflated, which can then be displaced by an azide to give a 2‐azido‐β‐ D ‐mannoside.…”

Section: Methodsmentioning

confidence: 99%

Chemical Synthesis and Immunological Properties of Oligosaccharides Derived from the Vegetative Cell Wall of Bacillus anthracis

Vasan¹,

Rauvolfová²,

Wolfert³

et al. 2008

ChemBioChem

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Bacillus anthracis vaccine candidate: Sera of rabbits exposed to live and irradiated-killed spores of B. anthracis Sterne 34F2 or immunized with B. anthracis polysaccharide conjugated to KLH elicited antibodies that recognize isolated polysaccharide and two synthetic trisaccharides providing a proof-of-concept step in the development of vegetative and spore-specific reagents for detection and targeting of non-protein structures of B. anthracis.

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Section: Methodsmentioning

confidence: 99%

Chemical Synthesis and Immunological Properties of Oligosaccharides Derived from the Vegetative Cell Wall of Bacillus anthracis

Vasan¹,

Rauvolfová²,

Wolfert³

et al. 2008

ChemBioChem

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“…In the alternative route [159,195,1961 a P-glucopyranoside is synthesized first, followed by azide-displacement at C-2 to provide the 2-azido-2-deoxy-Pmannopyranoside unit in a process as reviewed for the parent compound in Section 13.2.2.…”

Section: -Acetamido-2-deoxy-~-~-mannopyranosidesmentioning

confidence: 99%

Stereoselective Synthesis of β‐Mannosides

Pozsgay¹

2000

Carbohydrates in Chemistry and Biology

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IntroductionP-D-Mannopyranosyl residues are frequently found in oligosaccharides and glycoconjugates in living systems. This unit is omnipresent in N-linked glycoproteins that contain a pentasaccharide core (1) in which the P-linked mannose residue can carry additional sugars [I] (Scheme 1). P-Mannopyranose moieties are often part of the 0-specific polysaccharides (OSPs) of Gram-negative bacteria [2-8] and of bacterial capsular and em-polysaccharides [6,[9][10][11][12][13][14][15]. P-Linked mannopyranose is also a common residue in plant polysaccharides [ 161. Further examples of the occurrence of the P-mannosidic linkage are the glycosphingolipids in wheat flour [ 171 and in the freshwater bivalve Hyriopsis schlegelii [ 181. Interestingly, this residue is absent from mammalian glycolipids [19]. Cell-wall phosphomannans of yeasts contain linear chains of up to fourteen P-1,2-linked mannose residues [20, 211. P-Mannopyranose units also occur in secreted small molecules. Examples include the phospholipase inhibitor caloporoside [22] and free oligosaccharides detected in a patient with mannosidosis [23] and isolated from ripening tomatoes [24]. The related P-linked 2-acetamido-2deoxy-D-mannopyranose also frequently occurs in OSPs [ 8, 251 and in capsular polysaccharides [26-3 11. The corresponding mannuronic acid is present in the enterobacterial common antigen [32] and in other bacterial polysaccharides [6, 331.The occurrence of the 0-mannosyl unit in many biological systems creates a biological rationale for its synthesis. Whereas the simple methyl [34-381 and phenyl P-D-mannopyranoside [ 391 have been known for many years, the synthesis of complex oligosaccharides containing this unit is still a challenge for two reasons [40-441. First, the anomeric effect facilitates the formation of the 1,2-truns-mannopyranosyl (a) linkage thus it disfavors the P-linkage and, second, the 1,2-cis arrangement of the equatorial aglycone and the axial functionality at C-2 in P-mannopyranosides harbors repulsive steric effects [40]. Glycosyl donors with a participating group at 0 -2 and halide-ion catalytic conditions promote the exclusive formation of (Y man-Carbohydrates in Chemistry and Biology FHzOAc CHzOH HOH& 1 . Ag20.1, AcO & Br -t AcO 2.Ba(OWzb OAc 2 3 Scheme 2. + H O~O Ag2C03 ~ E@&&o, , CH2CI2 Bn OBn Yield: 64% c1 5 6 7 Scheme 3. 13 Stereoselective Synthesis of p-Mannosides 1 -55 to -30°C Br 13 Yield: 87% 14 Scheme 5. Ag silicate 0~~ -15 to25 OC Bn OMP CH,CI, + Br NPhth pphth Yield: 22% 15 16 17 Scheme 6.A more predictable approach to this problem has become possible by van Boeckel's recognition that an electron-withdrawing, acyl substituent at 0-4 of mannosyl donors promotes P-selectivity whereas such substituents at 0 -3 and 0-6 reduce it [52]. Highly reactive donor-acceptor combinations seem exempt from this rule [69, 701-silver silicate-promoted condensation of the mannosyl donor 13 with n-octanol affords the P-linked mannoside 14 in excellent yield even without an acyl substituent at 0-4 (Scheme 5) [69]. Paulsen's acti...

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“…[9] It is also a frequently occurring glycosyl residue in capsular polysaccharides and lipopolysaccharides of bacteria [10,11] and microorganisms. [12] The b-ManNAc units in some saccharides have potent implications in the virulence and pathogenicity of some bacteria. [10] These and several other examples of obvious physiologic activity of compounds containing ManNAc are the main reasons why the synthesis of its derivatives still remains a great challenge in carbohydrate chemistry.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Acylated Methyl 2‐Acetamido‐2‐Deoxy‐α‐D‐Mannopyranosides

Petrović

Car

Prugovečki

et al. 2006

Journal of Carbohydrate Chemistry

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2-Acetamido-2-deoxy-b-D-mannopyranose (1) was glycosylated by the Fischer method using an acidic ion-exchange resin as the catalyst to give a-methyl glycoside 2. Selective pivaloylations of methyl 2-acetamido-2-deoxy-a-D-mannopyranoside (2) have been studied under various reaction conditions. Two partially pivaloylated products were submitted to additional acetylations. All structures were established by NMR spectroscopy. Structure of the methyl 2-acetamido-2-deoxy-3,6-di-O-pivaloyl-a-D-mannopyranoside (4) was determined by X-ray analysis.

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Synthesis of an artificial antigen that corresponds to a disaccharide repeating unit of the capsular polysaccharide of Haemophilus influenzae type d. A facile synthesis of methyl 2-acetamido-2-deoxy-β- d -mannopyranoside

Cited by 36 publications

References 18 publications

Chemical Synthesis and Immunological Properties of Oligosaccharides Derived from the Vegetative Cell Wall of Bacillus anthracis

Chemical Synthesis and Immunological Properties of Oligosaccharides Derived from the Vegetative Cell Wall of Bacillus anthracis

Stereoselective Synthesis of β‐Mannosides

Synthesis of Acylated Methyl 2‐Acetamido‐2‐Deoxy‐α‐D‐Mannopyranosides

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