A Comparative Study of BOP as a Coupling Agent Using Simultaneous Multiple Peptide Synthesis

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Title:A Comparative Study of BOP as a Coupling Agent Using Simultaneous Multiple Peptide Synthesis
Creators:
Ježek, Jan
Houghten, Richard A.
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 59, 3, pp. 691-706

Abstract

<p>A parallel simultaneous synthesis of multiple peptides was carried out in which the coupling agents BOP and DIPCI were compared. For peptides lacking Asn, no differences in average yield or RP HPLC purity were found. For peptides having Asn in their sequences, however, the yield and purity were significantly lower for BOP when compared to DIPCI. The addition of HOBt to BOP mediated couplings did not lead to improved results. In fact, BOP condensations without HOBt gave, on average, slightly purer peptides. Comparing the results for peptides prepared with BOP dissolved in DMF, NMP, or NMP + 20% DMSO, NMP afforded the best and DMF the worst results, but the differences were not significant. Peptides prepared using BOP, combined with in situ neutralization, were obtained both in higher yield and purity when compared with classical neutralization. In all BOP mediated couplings, peptides with Asn were obtained in lower yield and purity than peptides without Asn. FAB MS and amino acid analysis revealed that the side products are peptides with deleted Asn.

Title:A Comparative Study of BOP as a Coupling Agent Using Simultaneous Multiple Peptide Synthesis
Creators:
Ježek, Jan
Houghten, Richard A.
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:59
Number:3
Page Range:pp. 691-706
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19940691UNSPECIFIED
ID Code:492
Item Type:Article
Deposited On:06 Feb 2009 17:01
Last Modified:06 Feb 2009 16:01

Citation

Ježek, Jan; Houghten, Richard A. (1994) A Comparative Study of BOP as a Coupling Agent Using Simultaneous Multiple Peptide Synthesis. Collection of Czechoslovak Chemical Communications, 59 (3). pp. 691-706. ISSN 0010-0765

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