Efficient introduction of protected guanidines in BOC solid phase peptide synthesis

Organic Letters

Volumn 3, Issue 15, 2001, Pages 2341-2344

  Zhang, Yongda ^a   Kennan, Alan J ^a  

^a Department of Ecosystem Science and Sustainability   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; AMINO ACID; FLUORENE DERIVATIVE; FORMIC ACID DERIVATIVE; GUANIDINE DERIVATIVE; N(ALPHA) FLUORENYLMETHYLOXYCARBONYLAMINO ACIDS; N(ALPHA)-FLUORENYLMETHYLOXYCARBONYLAMINO ACIDS; PEPTIDE; PYRAZOLE DERIVATIVE; SULFONAMIDE; T BUTYLOXYCARBONYL GROUP; T-BUTYLOXYCARBONYL GROUP;

AMINO ACID SEQUENCE; ARTICLE; CHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOLECULAR GENETICS; SYNTHESIS;

AMINES; AMINO ACID SEQUENCE; AMINO ACIDS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FLUORENES; FORMIC ACID ESTERS; GUANIDINES; MOLECULAR SEQUENCE DATA; PEPTIDES; PYRAZOLES; SULFONAMIDES;

EID: 0035954866     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016139b     Document Type: Article

References (26)

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17. For example, use of N-Boc-α-amino-γ-N-tosylguanidinobutyric acid gave little or no desired product even using extended coupling times and excess reagents.
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21. See Supporting Information for experimental details.
22. 2; 3:1 ethyl acetate:hexane) to afford pure product.
23. Peptides were synthesized according to standard Boc protocols, employing the in situ neutralization procedure developed by Kent: Schnoelzer, M.; Alewood, P.; Jones, A.; Alewood, D.; Kent, S. B. H. Int. J. Pept. Protein Res. 1992, 40, 180-193.
24. Functionalization of all resin-bound amines was verified by the Kaiser test. Kaiser, E.; Colescott, R. L.; Bossinger, C. D.; Cook, P. I. Anal. Biochem. 1970, 34, 595-598.
25. The identity of each peptide was confirmed by electrospray mass spectrometry of a sample purified by reverse-phase HPLC. See Supporting Information.
26. One-letter abbreviations: A = alanine, E = glutamic acid, K = lysine, L = leucine, N = aspartic acid, Q = glutamine, X = α-aminobutyric acid.