Synthesis of tri-functionalized MMP2 FRET probes using a chemo-selective and late-stage modification of unprotected peptides

2017 ◽  
Vol 15 (8) ◽  
pp. 1792-1800 ◽  
Author(s):  
Sean Oriana ◽  
Ye Cai ◽  
Jeffrey W. Bode ◽  
Yoko Yamakoshi
Keyword(s):  
Peptide Synthesis ◽  
Late Stage ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Peptide Sequence ◽  
Hydroxylamine Derivative ◽  
Natural Peptide

A polymeric FRET probe for the detection of MMP2 was prepared using a new N-hydroxylamine derivative of lysine, which was successfully incorporated into the natural peptide sequence by solid phase peptide synthesis, allowing dual orthogonal ligations of the fully unprotected peptides.

scholarly journals Harnessing polarity and viscosity to identify green binary solvent mixtures as viable alternatives to DMF in solid-phase peptide synthesis

2021 ◽  
Author(s):  
Vincent Martin ◽  
Sandip Jadhav ◽  
Peter H. G. Egelund ◽  
Raphael Liffert ◽  
Henrik Johansson Castro ◽  
...  
Keyword(s):  
Pharmaceutical Industry ◽  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Peptide Sequence ◽  
Binary Solvent ◽  
Solvent Mixtures ◽  
Binary Solvent Mixtures

Solid-phase peptide synthesis (SPPS) enables routine synthesis of virtually any type of peptide sequence and is the preferred method for peptide synthesis in academia and the pharmaceutical industry alike. Still,...

scholarly journals Synthesis of secondary and tertiary amides without coupling agents from amines and potassium acyltrifluoroborates (KATs)

2020 ◽  
Vol 11 (29) ◽  
pp. 7609-7614 ◽  
Author(s):  
Anne Schuhmacher ◽  
Tomoya Shiro ◽  
Sarah J. Ryan ◽  
Jeffrey W. Bode
Keyword(s):  
Peptide Synthesis ◽  
Late Stage ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Bioactive Molecules ◽  
Coupling Agents ◽  
Oxidative Amidation ◽  
Tertiary Amides

Oxidative amidation of potassium acyltrifluoroborates (KATs) and amines via trifluoroborate iminiums (TIMs) delivers amides without coupling agents. This unusual approach to amides can be applied for the late-stage modification of bioactive molecules and for solid-phase peptide synthesis.

scholarly journals Late-stage peptide C–H alkylation for bioorthogonal C–H activation featuring solid phase peptide synthesis

2019 ◽  
Vol 10 (1) ◽  
Author(s):  
Alexandra Schischko ◽  
Nikolaos Kaplaneris ◽  
Torben Rogge ◽  
Giedre Sirvinskaite ◽  
Jongwoo Son ◽  
...  
Keyword(s):  
Peptide Synthesis ◽  
Late Stage ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis

A Strategy for Thioamide Incorporation During Fmoc Solid-Phase Peptide Synthesis with Robust Stereochemical Integrity

2019 ◽  
Author(s):  
luis camacho III ◽  
Bryan J. Lampkin ◽  
Brett VanVeller
Keyword(s):  
Amino Acid ◽  
Functional Groups ◽  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Side Chains ◽  
Amino Acid Side Chains ◽  
Peptide Elongation

We describe a method to protect the sensitive stereochemistry of the thioamide—in analogy to the protection of the functional groups of amino acid side chains—in order to preserve the thioamide moiety during peptide elongation.<br>

Analytical Methods for Solid Phase Peptide Synthesis

2004 ◽  
Vol 8 (4) ◽  
pp. 291-301 ◽  
Author(s):  
Giuseppina Sabatino ◽  
Mario Chelli ◽  
Alberto Brandi ◽  
Anna Papini
Keyword(s):  
Peptide Synthesis ◽  
Analytical Methods ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis

Fmoc Solid Phase Peptide Synthesis

1999 ◽  
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Peptide Chain ◽  
Standard Approach ◽  
Side Chain ◽  
Complex Structures ◽  
Protein Conjugation ◽  
Chemoselective Ligation ◽  
Routine Production

In the years since the publication of Atherton and Sheppard's volume, the technique of Fmoc solid-phase peptide synthesis has matured considerably and is now the standard approach for the routine production of peptides. The basic problems outstanding at the time of publication of this earlier work have now been, for the most part, solved. As a result, innovators in the field have focussed their efforts to develop methodologies and chemistry for the synthesis of more complex structures. The focus of this new volume is much broader, and covers not only the essential procedures for the production of linear peptides but also more advanced techniques for preparing cyclic, side-chain modified, phospho- and glycopeptides. Many other methods also deserving attention have been included: convergent peptide synthesis; peptide-protein conjugation; chemoselective ligation; and chemoselective purification. The difficult preparation of cysteine and methionine-containing peptides is also covered, as well as methods for overcoming aggregation during peptide chain assembly and a survey of available automated instrumentation.

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