Combinatorial chemistry of piperidine based carbohydrate mimics

Tetrahedron Letters

Volumn 38, Issue 32, 1997, Pages 5697-5700

  Byrgesen, Elisabeth ^a   Nielsen, John ^a   Willert, Marianne ^b   Bols, Mikael ^b  

^a TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

^b AARHUS UNIVERSITY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDASE INHIBITOR; PIPERIDINE DERIVATIVE;

ARTICLE; CARBOHYDRATE SYNTHESIS; IN VITRO STUDY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METHODOLOGY; REACTION ANALYSIS;

EID: 0030817956     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01249-5     Document Type: Article

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16. 2)).
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20. HPLC was performed on a Chiralpac AD coloumn (cellulose triacetate) using EtOH as mobile phase, a flow of 0.5 ml/min and measuring of absorption at 390 nm.
21. Baláspiri, L.; Penke, B.; Petres, J.; Kovács, K. Monatshefte für Chemie 1970, 101, 1177-1183.
22. Ponnusamy, E.; Fotadar, U.; Spisni, A.; Fiat, D. Synthesis 1986, 48-49.
23. 4-Methyl Benzhydrylamine resin from Novabiochem is used with a substitutionlevel of 0.46 mmole/g.
24. Carpino, L. A. J. Am. Chem. Soc. 1993, 115, 4397-4398.
25. MBHA-resin (900 mg ) was split in three. Each portion was coupled for two hours with a monomer 8, 9 or 10 (3eq.) using HATU (2.5 eq) and DIEA (6eq) in 3 ml of DMF/DCM (1:1). The monomer was prereacted with HATU and DIEA for 2 min. to avoid formation of byproducts (Gausepohl, H; Pieles, U; Frank, R. W. Peptides, Chemistry and Biology, 1992, 523-524.) After reaction, the resin was washed with 3×2 ml DMF and 3×2 ml DCM. The three portions of resin were mixed, treated with 50% TFA/DCM (2×10min) to remove the BOC protecting group and split into three. The three fractions were reacted as described above with respectively 8, 9 and 10, washed, mixed, deprotected, split and reacted a last time with the tree monomers.
26. It is not possible to follow the reaction using the Kaiser-test, as this is inaccurate for secondary amines.
27. Stewart, J. M.; Young, J. D. Solid phase peptide synthesis, Pierce Chemical Company, sec. Ed., 1984, 89.
28. 2O) as mobile phase and a flow of 1 ml/min. The sublibraries were deprotected and reacted in DMF with Sanger's reagent and DIEA. After cleavage of the resin, the HPLC were recorded at 390 nm.
29. Each of the sub-libraries were reacted with Sanger's reagent and analyzed by LC-UV/MS. As monomer 9 and 10 have the same mass in total 4 different masses (516.23, 532.23, 548.22 and 564.22) were expected, and with 3 different masses in each sub-library. Within the chromatograms of the three individual sub-libraries, peaks having the expected masses were identified in all cases.