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Availabilty of phenylisothiocyanate for the amino acid sequence/configuration determination of peptides containing D/L-amino acids

✍ Scribed by Kazuhiro Imai; Hirokazu Matsunaga; Tomofumi Santa; Hiroshi Homma

Publisher
John Wiley and Sons
Year
1995
Tongue
English
Weight
213 KB
Volume
9
Category
Article
ISSN
0269-3879

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✦ Synopsis

A potential use for phenylisothiocyanate (PITC), the most popular Edman reagent, is presented for analysis of the amino acid sequence and configuration in peptides containing oiL-amino acids. After derivatization with PITC of the A'-terminal amino acid (L-TY~) of an enkephalin analogue, [D-Ala', o-Leu5]-enkephaIin, followed by cleavage/cyclization with trifluoroacetic acid at 50 "C for 5 min, the liberated 2-anilino-5-thiazolinone-~-Tyr (ATZ-L-Tyr) was further treated with 20% aqueous trifluoroacetic acid at 50Β°C for 10min. The resultant phenylthiohydantoin (PTH)-L-Tyr was then separated on a chiral stationary phase (a penylcarbamoylated cyclodextrin column), retaining its configuration. The residual sequence and configurations of the peptide (D-Aia-Gly-r,-Phe-o-Leu) were also delermined by separating the corresponding PTH-Dor L-amino acids on chiral columns. This method may be applicable to an automatic Edman sequence analyzer for the configuration determination of peptides containing DiL-amino acids.

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