Literature DB >> 20931985

Efficient microwave-assisted synthesis of human islet amyloid polypeptide designed to facilitate the specific incorporation of labeled amino acids.

Peter Marek1, Ann Marie Woys, Kelvin Sutton, Martin T Zanni, Daniel P Raleigh.   

Abstract

A cost-efficient, time-reducing solid-phase synthesis of the amyloidogenic, 37 residue islet amyloid polypeptide (IAPP) is developed using two pseudoprolines (highlighted blue in sequence) in combination with microwave technology. A yield twice that obtained with conventional syntheses is realized. The utility of this protocol is demonstrated by the synthesis of a (13)C(18)O-labeled Ser-20 IAPP variant, a prohibitively expensive and chemically challenging site to label via other protocols. TEM analysis shows the peptide forms normal amyloid (abstract image).

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Year:  2010        PMID: 20931985      PMCID: PMC3052696          DOI: 10.1021/ol101981b

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  19 in total

1.  Two-dimensional IR spectroscopy and isotope labeling defines the pathway of amyloid formation with residue-specific resolution.

Authors:  Sang-Hee Shim; Ruchi Gupta; Yun L Ling; David B Strasfeld; Daniel P Raleigh; Martin T Zanni
Journal:  Proc Natl Acad Sci U S A       Date:  2009-04-03       Impact factor: 11.205

2.  Solid-phase synthesis of difficult peptide sequences at elevated temperatures: a critical comparison of microwave and conventional heating technologies.

Authors:  Bernadett Bacsa; Kata Horváti; Szilvia Bõsze; Fritz Andreae; C Oliver Kappe
Journal:  J Org Chem       Date:  2008-08-27       Impact factor: 4.354

3.  Widespread amyloid deposition in transplanted human pancreatic islets.

Authors:  Gunilla T Westermark; Per Westermark; Christian Berne; Olle Korsgren
Journal:  N Engl J Med       Date:  2008-08-28       Impact factor: 91.245

4.  Purification and characterization of a peptide from amyloid-rich pancreases of type 2 diabetic patients.

Authors:  G J Cooper; A C Willis; A Clark; R C Turner; R B Sim; K B Reid
Journal:  Proc Natl Acad Sci U S A       Date:  1987-12       Impact factor: 11.205

5.  Incorporation of pseudoproline derivatives allows the facile synthesis of human IAPP, a highly amyloidogenic and aggregation-prone polypeptide.

Authors:  Andisheh Abedini; Daniel P Raleigh
Journal:  Org Lett       Date:  2005-02-17       Impact factor: 6.005

6.  Limiting racemization and aspartimide formation in microwave-enhanced Fmoc solid phase peptide synthesis.

Authors:  Stacey A Palasek; Zachary J Cox; Jonathan M Collins
Journal:  J Pept Sci       Date:  2007-03       Impact factor: 1.905

7.  Islet amyloid deposition limits the viability of human islet grafts but not porcine islet grafts.

Authors:  K J Potter; A Abedini; P Marek; A M Klimek; S Butterworth; M Driscoll; R Baker; M R Nilsson; G L Warnock; J Oberholzer; S Bertera; M Trucco; G S Korbutt; P E Fraser; D P Raleigh; C B Verchere
Journal:  Proc Natl Acad Sci U S A       Date:  2010-02-16       Impact factor: 11.205

8.  Residue-specific, real-time characterization of lag-phase species and fibril growth during amyloid formation: a combined fluorescence and IR study of p-cyanophenylalanine analogs of islet amyloid polypeptide.

Authors:  Peter Marek; Sudipta Mukherjee; Martin T Zanni; Daniel P Raleigh
Journal:  J Mol Biol       Date:  2010-06-01       Impact factor: 5.469

9.  Amyloid formation results in recurrence of hyperglycaemia following transplantation of human IAPP transgenic mouse islets.

Authors:  J Udayasankar; K Kodama; R L Hull; S Zraika; K Aston-Mourney; S L Subramanian; J Tong; M V Faulenbach; J Vidal; S E Kahn
Journal:  Diabetologia       Date:  2008-11-11       Impact factor: 10.122

10.  Rapid deposition of amyloid in human islets transplanted into nude mice.

Authors:  P Westermark; D L Eizirik; D G Pipeleers; C Hellerström; A Andersson
Journal:  Diabetologia       Date:  1995-05       Impact factor: 10.122

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  48 in total

1.  Deamidation accelerates amyloid formation and alters amylin fiber structure.

Authors:  Emily B Dunkelberger; Lauren E Buchanan; Peter Marek; Ping Cao; Daniel P Raleigh; Martin T Zanni
Journal:  J Am Chem Soc       Date:  2012-07-17       Impact factor: 15.419

2.  Analysis of the Amyloidogenic Potential of Pufferfish (Takifugu rubripes) Islet Amyloid Polypeptide Highlights the Limitations of Thioflavin-T Assays and the Difficulties in Defining Amyloidogenicity.

Authors:  Amy G Wong; Chun Wu; Eleni Hannaberry; Matthew D Watson; Joan-Emma Shea; Daniel P Raleigh
Journal:  Biochemistry       Date:  2016-01-13       Impact factor: 3.162

3.  Amyloidogenicity and cytotoxicity of des-Lys-1 human amylin provides insight into amylin self-assembly and highlights the difficulties of defining amyloidogenicity.

Authors:  Kyung-Hoon Lee; Alexander Zhyvoloup; Daniel Raleigh
Journal:  Protein Eng Des Sel       Date:  2019-12-13       Impact factor: 1.650

4.  Evolutionary Adaptation and Amyloid Formation: Does the Reduced Amyloidogenicity and Cytotoxicity of Ursine Amylin Contribute to the Metabolic Adaption of Bears and Polar Bears?

Authors:  Rehana Akter; Andisheh Abedini; Zachary Ridgway; Xiaoxue Zhang; Joel Kleinberg; Ann Marie Schmidt; Daniel P Raleigh
Journal:  Isr J Chem       Date:  2016-12-19       Impact factor: 3.333

5.  2DIR spectroscopy of human amylin fibrils reflects stable β-sheet structure.

Authors:  Lu Wang; Chris T Middleton; Sadanand Singh; Allam S Reddy; Ann M Woys; David B Strasfeld; Peter Marek; Daniel P Raleigh; Juan J de Pablo; Martin T Zanni; James L Skinner
Journal:  J Am Chem Soc       Date:  2011-09-15       Impact factor: 15.419

6.  Analysis of Amylin Consensus Sequences Suggests That Human Amylin Is Not Optimized to Minimize Amyloid Formation and Provides Clues to Factors That Modulate Amyloidogenicity.

Authors:  Daeun Noh; Rebekah L Bower; Debbie L Hay; Alexander Zhyvoloup; Daniel P Raleigh
Journal:  ACS Chem Biol       Date:  2020-06-03       Impact factor: 5.100

7.  Matrix Metalloproteinase-9 Protects Islets from Amyloid-induced Toxicity.

Authors:  Daniel T Meier; Ling-Hsien Tu; Sakeneh Zraika; Meghan F Hogan; Andrew T Templin; Rebecca L Hull; Daniel P Raleigh; Steven E Kahn
Journal:  J Biol Chem       Date:  2015-10-19       Impact factor: 5.157

8.  Mechanism of IAPP amyloid fibril formation involves an intermediate with a transient β-sheet.

Authors:  Lauren E Buchanan; Emily B Dunkelberger; Huong Q Tran; Pin-Nan Cheng; Chi-Cheng Chiu; Ping Cao; Daniel P Raleigh; Juan J de Pablo; James S Nowick; Martin T Zanni
Journal:  Proc Natl Acad Sci U S A       Date:  2013-11-11       Impact factor: 11.205

9.  Amyloid formation in heterogeneous environments: islet amyloid polypeptide glycosaminoglycan interactions.

Authors:  Hui Wang; Ping Cao; Daniel P Raleigh
Journal:  J Mol Biol       Date:  2012-11-12       Impact factor: 5.469

10.  Sterol Structure Strongly Modulates Membrane-Islet Amyloid Polypeptide Interactions.

Authors:  Xiaoxue Zhang; Erwin London; Daniel P Raleigh
Journal:  Biochemistry       Date:  2018-03-12       Impact factor: 3.162

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