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A New Reagent for the Cleavage of NPS‐Amino Protecting Groups in Peptide Synthesis
Author(s) -
Juillerat Marcel,
Pierre Bargetzi J.
Publication year - 1976
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19760590315
Subject(s) - chemistry , reagent , nucleophile , combinatorial chemistry , protecting group , peptide synthesis , nitro , alkyl , amino acid , peptide , solubility , organic chemistry , benzoic acid , solid phase synthesis , catalysis , biochemistry
The value of several reagents capable of removing quantitatively the α‐amino protecting group of NPS‐aminoacyl‐ or peptidyl‐derivatives is assessed, by comparison with the reagents currently used, i.e. hydrogen chloride, RS – ‐nucleophiles or alkyl thioamides, especially with regard to reaction specificity and end‐product solubility. New reagents proposed, 3‐nitro‐4‐mercapto‐benzoic acid, and its methyl ester, appear to optimize the numerous, and often competing, requirements. These were probed, under conditions suitable for both conventional and solid‐phase methods, on a series of model compounds, including diversely protected amino acids and short peptides, as well as for the actual synthesis of a triacontapeptide by the stepwise, solid‐phase approach.