Nα-mercaptobenzylamine-assisted chemical ligation

Organic Letters

Volumn 2, Issue 1, 2000, Pages 23-26

  Offer, John ^a   Dawson, Philip E ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYSTEINE; PEPTIDE; THIOL DERIVATIVE;

ARTICLE; CHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; KINETICS; SYNTHESIS;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYSTEINE; KINETICS; PEPTIDES; SULFHYDRYL COMPOUNDS;

EID: 0033657692     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991184t     Document Type: Article

References (30)

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17. 2-Thiobenzaldehyde was prepared from 2-thiobenzyl alcohol (Lancaster) by the method of: Kasmai, H. S.; Mischke, S. G. Synthesis 1989, 763-764. The trityl protection was added as described in: Annis, I.; Chen, L.; Barany, G. J. Am. Chem. Soc. 1998, 120, 7226-7238. The reductive amination of the peptide was initially problematic, especially for glycine, because of side reactions of thiosalicaldehydes with primary amines. Corrigan, M. F.; Rae, I. D.; West, B. O. Aust. J. Chem. 1978, 31, 587-594. Very low yields of the desired monoalkylated material were obtained; therefore, the thiol was protected with trityl to give, after reductive amination onto the resin-bound peptide, monoalkylated product in reasonable yield (50% after preparative HPLC).
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19. Electrospray ionization MS data for products shown in Table 1: LYRAG(Mba)GRANK M, obsd 1227 (calcd 1227.5); LYRAG(Mba)-ARANK M, obsd 1242.5 (calcd 1242.5); LYRAF(Mba)GRANK M, obsd: 1319 (calcd 1318.6); LYRAG(Mba)VRANK M, obsd 1268.5 (calcd 1269.5).
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