For some years our laboratory has been interested in the synthesis of cord factor (6,6'-di-O-mycoloyl-~,#-trehalose) and cord-factor analogues, and several syntheses of this class of biologically impo~ant compounds have been described'-', involving 2,3,4,2',3' ,4'-hexa-O-benzyl-~,~-trehalose (2) as
Gram-scale synthesis of α,α-trehalose 6-monophosphate and α,α-trehalose 6,6′-diphosphate
✍ Scribed by Tor E.C.L. Rønnow; Morten Meldal; Klaus Bock
- Publisher
- Elsevier Science
- Year
- 1994
- Tongue
- English
- Weight
- 428 KB
- Volume
- 260
- Category
- Article
- ISSN
- 0008-6215
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📜 SIMILAR VOLUMES
cY,cu'-Trehalose, when dried to a moisture content of ca. 5% from aqueous sodium phosphate buffer (with an initial pH I 5.5), produces, after warming, a mixture containing the four isomeric monophosphate esters which can be isolated by anion-exchange chromatography. Their structures were deduced fro
6-Deoxy-6-mycoloylamino-a,a-trehalose, a biologically active derivative of 6,6'-di-0-mycoloyl-a,a-trehalose (TDM), andN-acetyl-6-O-(aminoacyl)-muramoyl dipeptide (MDP) were joined chemically by a succinic acid unit. The compounds synthesized showed activities that are characteristic of both TDM and
11. and Raman spectra of solid a,a-trehalose and a,a-trehalose-2,3,4.6,6-6,, in the C-H and C-D stretching regions are recorded. The experimental data are reproduced satisfactorily by normal co-ordinate and i.r. absorption intensity calculations which take into account the specific interactions of e
6,6'Di-O-mycoloyl-beta,beta-trehalose (beta,beta-TDM) and 6,6'-di-O-mycoloyl-alpha,beta-trehalose (alpha,beta-TDM) were synthesized and their toxicity and ability to activate peritoneal macrophages in situ were examined in mice, in comparison with 6,6'-di-O-mycoloyl-alpha,alpha-trehalose (TDM). Both