Further Studies on the Side Reactions Associated with Use of Nπ- Benzyloxymethylhistidine

Author(s): Kumiko Yoshizawa-Kumagaye, Takehiro Ishizu, Shuji Isaka, Masaji Tamura, Rumi Okihara, Yuji Nishiuchi, Terutoshi Kimura.

Journal Name: Protein & Peptide Letters

Volume 12 , Issue 6 , 2005

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The use of Nα-tert.-butyloxycarbonyl-Nπ-benzyloxymethylhistidine [Boc-His(Bom)] in peptide synthesis results in a serious level of side products arising from the generation of formaldehyde during the HF cleavage reaction. In particular, when treating a His(Bom)-containing peptide having Cys at the N-terminus by HF, this leads to almost complete conversion of the Cys-peptide to thiazolidyl (Thz)-peptide unless precautions are taken. Also, the reaction of formaldehyde with the N-terminal Trp and the N-methylanthranyl (Nma) group was found to produce tetrahydro-β- carboline and dihydroquinazolin derivatives, respectively, upon isolation from HF mixtures. The addition of cysteine as a scavenger in HF proved to be effective for suppressing modification arising from the generation of formaldehyde.

Keywords: benzyloxymethyl (bom), dihydroqunazolin, formaldehyde, hf, n-methylanthranyl (nma), tetrahydro carboline

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Article Details

Year: 2005
Page: [579 - 582]
Pages: 4
DOI: 10.2174/0929866054395789
Price: $65

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