Calcium-promoted hydrolysis of N-acylureas allows mild release of peptides anchored with Dpr(Phoc) linker to hydrophilic resins

Tetrahedron Letters

Volumn 38, Issue 26, 1997, Pages 4549-4552

  Pascal, Robert ^a,b   Sola, Régine ^a,b  

^a CNRS   (France)

^b CCIPE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CALCIUM CHLORIDE; PEPTIDE; RESIN;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DERIVATIZATION; DRUG SYNTHESIS; HYDROLYSIS; REACTION ANALYSIS;

EID: 0030991484     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00973-8     Document Type: Article

References (26)

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11. 2 was purchased from Rapp Polymere, D-7400 Tubingen, Germany.
12. 2O washes.
13. R 14.1 min Bz-Leu-Phe; PhOH and Bz-Leu-Phe determination was performed after calibration with standard solutions of pure materials.
14. The small experimental effect on the activation step (entries 1 and 2) is mostly accounted for by the two opposite effects of ionic strength and pH, as shown by comparison of entries 1 with 3, and 3 with 4, respectively.
15. R 14.5 min for Bz-L-Leu-D-Phe [assumed to have the same retention time as the enantiomer Bz-D-Leu-L-Phe observed in the diastereomeric mixture that we intentionally prepared by coupling Bz-L-Leu-OSu with L-Phe (suspension in DMF) in the presence of excess DIEA].
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19. 2 (entry 17).
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24. - ions required for complete cleavage as fast as they are used by peptide release.
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