Use of Alloc-amino acids in solid-phase peptide synthesis. Tandem deprotection-coupling reactions using neutral conditions

Tetrahedron Letters

Volumn 38, Issue 41, 1997, Pages 7275-7278

  Thieriet, Nathalie ^a,b   Alsina, Jordi ^a   Giralt, Ernest ^a   Guibé, François ^b   Albericio, Fernando ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b UNIVERSITÉ PARIS SUD   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID SYNTHESIS; ARTICLE; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS;

EID: 0030657857     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01690-0     Document Type: Article

References (39)

1. Abbreviations used in this article: AAA, amino acid analysis; AB, 3-(4-hydroxymethylphenoxy) propionic acid; Act, activating groups; All, allyl; Alloc, allyloxycarbonyl; Allocam, allyloxycarbonylaminomethyl; Boc, t-butoxycarbonyl; Bz1, benzyl; t-Bu, t-butyl; DIEA, N,N-diisopropylethylamine; DKP, diketopiperazine; Fm, 9-fluorenylmethyl; Fmoc, 9-fluorenylmethoxycarbonyl; HMPB, 4-(4-hydroxymethyl-3-methoxyphenoxy)-butyric acid; HPLC, high performance liquid chromatography; HOAc, acetic acid; Ind, indole; Im, imidazole; NCA, N-carboxyanhydride; PAL, 5-(4-aminomethyl-3,5-dimethoxyphenoxy)valeric acid; PEG-PS, polyethylene glycol-polystyrene graft; PyAOP, 7-azabenzotriazol-1-yl-oxytris(pyrrolidino)phosphonium hexafluorophosphate; PyBOP, benzotriazol-1-yl-oxytris(pyrrolidino)phosphonium hexafluorophosphate; SPPS, solid-phase peptide synthesis; TFA, trifluoroacetic acid; Trt, triphenylmethyl (trityl). Amino acid denotes L-configuration unless otherwise noted.
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27. Kates, S. A.: Albericio, F., unpublished results.
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30. tBu solid-phase peptide synthesis was as follows: Swelling of the resin by washing with DMF (3×1 min), removal of the Fmoc group with piperidine-DMF (2:8) (2×1min, 1×10 min), washing with DMF (5×1min). Fmoc-AA-OH and HOAt (3 fold excess relative to the amino function in both cases) were added as a solution in DMF followed by DIPCDI (3 equiv.). The mixture was left 60 min and then filtered, and washed with DMF (5×1 min).
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39. These results compare favorably with the previous reported method (see ref. 15b), because the removal of Alloc group does not involved the presence of acids, and therefore there is not risk of premature cleavage of the peptide from the resin.