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Total Chemical Synthesis of a Heterodimeric Interchain Bis-Lactam-Linked Peptide : Application to an Analogue of Human Insulin-Like Peptide 3
Joint Authors
Separovic, Frances
Wade, John D.
Gardiner, James
Hossain, Mohammed Akhter
Scanlon, Denis B.
Karas, John
Shabanpoor, Fazel
Source
International Journal of Peptides
Issue
Vol. 2013, Issue 2013 (31 Dec. 2013), pp.1-8, 8 p.
Publisher
Hindawi Publishing Corporation
Publication Date
2013-10-28
Country of Publication
Egypt
No. of Pages
8
Main Subjects
Abstract EN
Nonreducible cystine isosteres represent important peptide design elements in that they can maintain a near-native tertiary conformation of the peptide while simultaneously extending the in vitro and in vivo half-life of the biomolecule.
Examples of these cystine mimics include dicarba, diselenide, thioether, triazole, and lactam bridges.
Each has unique physicochemical properties that impact upon the resulting peptide conformation.
Each also requires specific conditions for its formation via chemical peptide synthesis protocols.
While the preparation of peptides containing two lactam bonds within a peptide is technically possible and reported by others, to date there has been no report of the chemical synthesis of a heterodimeric peptide linked by two lactam bonds.
To examine the feasibility of such an assembly, judicious use of a complementary combination of amine and acid protecting groups together with nonfragment-based, total stepwise solid phase peptide synthesis led to the successful preparation of an analogue of the model peptide, insulin-like peptide 3 (INSL3), in which both of the interchain disulfide bonds were replaced with a lactam bond.
An analogue containing a single disulfide-substituted interchain lactam bond was also prepared.
Both INSL3 analogues retained significant cognate RXFP2 receptor binding affinity.
American Psychological Association (APA)
Karas, John& Shabanpoor, Fazel& Hossain, Mohammed Akhter& Gardiner, James& Separovic, Frances& Wade, John D.…[et al.]. 2013. Total Chemical Synthesis of a Heterodimeric Interchain Bis-Lactam-Linked Peptide : Application to an Analogue of Human Insulin-Like Peptide 3. International Journal of Peptides،Vol. 2013, no. 2013, pp.1-8.
https://search.emarefa.net/detail/BIM-476862
Modern Language Association (MLA)
Karas, John…[et al.]. Total Chemical Synthesis of a Heterodimeric Interchain Bis-Lactam-Linked Peptide : Application to an Analogue of Human Insulin-Like Peptide 3. International Journal of Peptides No. 2013 (2013), pp.1-8.
https://search.emarefa.net/detail/BIM-476862
American Medical Association (AMA)
Karas, John& Shabanpoor, Fazel& Hossain, Mohammed Akhter& Gardiner, James& Separovic, Frances& Wade, John D.…[et al.]. Total Chemical Synthesis of a Heterodimeric Interchain Bis-Lactam-Linked Peptide : Application to an Analogue of Human Insulin-Like Peptide 3. International Journal of Peptides. 2013. Vol. 2013, no. 2013, pp.1-8.
https://search.emarefa.net/detail/BIM-476862
Data Type
Journal Articles
Language
English
Notes
Includes bibliographical references
Record ID
BIM-476862