A highly effective method for synthesis of N(ω)-substituted arginines as building blocks for Boc/Fmoc peptide chemistry

Tetrahedron Letters

Volumn 40, Issue 23, 1999, Pages 4439-4442

  Székely, Zoltán ^a   Zakhariev, Sotir ^a   Guarnaccia, Corrado ^a   Antcheva, Nikolinka ^a   Pongor, Sándor ^a  

^a INTERNATIONAL CENTRE FOR GENETIC ENGINEERING AND BIOTECHNOLOGY   (Italy)

Author keywords

Analogues; Guanylation; N( ) substituted arginine; SPPS

Indexed keywords

ALPHA AMINO ACID; AMIDINE; ARGININE DERIVATIVE; ARSENIC ACID DERIVATIVE; CARBONYL DERIVATIVE; GUANIDINE DERIVATIVE; OMEGA AMINO ACID; ORNITHINE DERIVATIVE;

AMINO ACID SYNTHESIS; ARTICLE; CRYSTALLIZATION; OPTICAL ROTATION; PEPTIDE SYNTHESIS; PROTEIN PURIFICATION; STEREOCHEMISTRY;

EID: 0033522964     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00767-4     Document Type: Article

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19. 2O; Buffer B=0.10%TFA/acetonitrile. Detection was at 214/264 nm
20. 2O; Buffer B=0.10%TFA/acetonitrile. Detection was at 214/264 nm
21. 4, filtered, and the solvent was removed in vacuo. The rest was used without further purification. (Orn-derivative. retention time (min), HPLC-purity (%): Boc, 25.6, 98.7; Z-, 26.3, > 99.1; Troc-. 26.2 , 97.9; Fmoc-, 28.3, 72.
22. 3 or diisopropylethylamine was used.
23. The regiospecific reaction of 1a with unprotected Orn (according to Gante, J., Angew. Chem., Int. Ed. Engl., 1967, 6(10), 862- 8) proceeds with low yield of 25-30 % 4 and requires purification by chromatography.
24. 2O.
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