New Effective Synthesis of (N-Acetyl- and N-Stearoyl-2-amino-2-deoxy-β-D-glucopyranosyl)-(1→4)-N-acetylnormuramoyl-L-2-aminobutanoyl-D-isoglutamine, Analogs of GMDP with Immunopotentiating Activity

[img]PDF - Authorized users only
Language: English
93Kb
Title:New Effective Synthesis of (N-Acetyl- and N-Stearoyl-2-amino-2-deoxy-β-D-glucopyranosyl)-(1→4)-N-acetylnormuramoyl-L-2-aminobutanoyl-D-isoglutamine, Analogs of GMDP with Immunopotentiating Activity
Creators:
Ledvina, Miroslav
Zyka, Daniel
Ježek, Jan
Trnka, Tomáš
Šaman, David
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 63, 4, pp. 577-589
Uncontrolled Keywords:Immunostimulators, Muramyl glycopeptides, Aminosugars, Oligosaccharides, Glycosides, Carbohydrates

Abstract

Ethyl 3,4,6-tri-<i>O</i>-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (<strong>5</strong>), prepared by benzylation of ethyl 2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (<strong>4</strong>), was transformed by reaction with bromine into 3,4,6-tri-<i>O</i>-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide (<strong>6</strong>). Thioglycoside <strong>5</strong> in the presence of methyl triflate and glycosylbromide <strong>6</strong> in the presence of silver triflate were used as glycosyl donors for condensation with benzyl 2-acetamido-3-<i>O</i>-allyl-6-<i>O</i>-benzyl-2-deoxy-α-D-glucopyranoside (<strong>7</strong>), to give benzyl 2-acetamido-3-<i>O</i>-allyl-6-<i>O</i>-benzyl-4-<i>O</i>-(3,4,6-tri-<i>O</i>-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-2-deoxy-α-D-glucopyranoside (<strong>8</strong>). Its reductive dephthaloylation with NaBH<sub>4</sub>/AcOH afforded benzyl 2-acetamido-3-<i>O</i>-allyl-4-<i>O</i>-(2-amino-3,4,6-tri-<i>O</i>-benzyl-2-deoxy-β-D-glucopyranosyl)- 6-<i>O</i>-benzyl-2-deoxy-α-D-glucopyranoside (<strong>11</strong>). Compound <strong>11</strong> was <i>N</i>-acylated to give benzyl 2-acetamido-4-<i>O</i>-(2-acylamino-3,4,6-tri-<i>O</i>-benzyl-2-deoxy-β-D-glucopyranosyl)-3-<i>O</i>-allyl-6-<i>O</i>-benzyl-2-deoxy-α-D-glucopyranosides (<strong>12a</strong>) or (<strong>12b</strong>). These compounds were converted into corresponding benzyl 2-acetamido-4-<i>O</i>-(2-acylamino-3,4,6-tri-<i>O</i>-benzyl-2-deoxy-β-D-glucopyranosyl)-6-<i>O</i>-benzyl-3-<i>O</i>-carboxymethyl-2-deoxy-α-D-glucopyranosides which, by condensation with H-L-Abu-D-isoGln(OBzl) followed by hydrogenolysis of protective benzyl groups, furnished glycopeptides <strong>16a </strong>and <strong>16b</strong>. Intramolecular O→N migration of the allyl protecting group followed by its reduction to the propyl residue by reaction of compound <strong>8</strong> with hydrazine or hydrazinium acetate, to give benzyl 2-acetamido-4-<i>O</i>-(3,4,6-tri-<i>O</i>-benzyl-2-deoxy-2-propylamino-β-D-glucopyranosyl)-6-<i>O</i>-benzyl-2-deoxy-α-D-glucopyranoside (<strong>9</strong>), is also described.

Title:New Effective Synthesis of (N-Acetyl- and N-Stearoyl-2-amino-2-deoxy-β-D-glucopyranosyl)-(1→4)-N-acetylnormuramoyl-L-2-aminobutanoyl-D-isoglutamine, Analogs of GMDP with Immunopotentiating Activity
Creators:
Ledvina, Miroslav
Zyka, Daniel
Ježek, Jan
Trnka, Tomáš
Šaman, David
Uncontrolled Keywords:Immunostimulators, Muramyl glycopeptides, Aminosugars, Oligosaccharides, Glycosides, Carbohydrates
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:63
Number:4
Page Range:pp. 577-589
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19980577UNSPECIFIED
ID Code:1323
Item Type:Article
Deposited On:06 Feb 2009 17:08
Last Modified:06 Feb 2009 16:08

Citation

Ledvina, Miroslav; Zyka, Daniel; Ježek, Jan; Trnka, Tomáš; Šaman, David (1998) New Effective Synthesis of (N-Acetyl- and N-Stearoyl-2-amino-2-deoxy-β-D-glucopyranosyl)-(1→4)-N-acetylnormuramoyl-L-2-aminobutanoyl-D-isoglutamine, Analogs of GMDP with Immunopotentiating Activity. Collection of Czechoslovak Chemical Communications, 63 (4). pp. 577-589. ISSN 0010-0765

Repository Staff Only: item control page