scholarly journals Build/Couple/Pair Strategy for the Synthesis of Stereochemically Diverse Macrolactams via Head-to-Tail Cyclization

2012 ◽  
Vol 14 (2) ◽  
pp. 89-96 ◽  
Author(s):  
Mark E. Fitzgerald ◽  
Carol A. Mulrooney ◽  
Jeremy R. Duvall ◽  
Jingqiang Wei ◽  
Byung-Chul Suh ◽  
...  
Keyword(s):  
Couple Pair ◽  
Head To Tail Cyclization

scholarly journals Spontaneous head-to-tail cyclization of unprotected linear peptides with the KAHA ligation

2015 ◽  
Vol 6 (8) ◽  
pp. 4889-4896 ◽  
Author(s):  
Florian Rohrbacher ◽  
Gildas Deniau ◽  
Anatol Luther ◽  
Jeffrey W. Bode
Keyword(s):  
Cyclic Peptides ◽  
Mechanistic Study ◽  
Coupling Reagents ◽  
Head To Tail Cyclization

The α-ketoacid–hydroxylamine (KAHA) ligation enables the direct cyclization of unprotected peptides upon cleavage, without coupling reagents or purification of precursors. We report the synthesis of a library of 24 cyclic peptides and a detailed mechanistic study.

Synthesis of Dichotomin A: Use of a Penicillamine-Derived Pseudoproline to Furnish Native Valine Residues

2015 ◽  
Vol 68 (4) ◽  
pp. 627 ◽  
Author(s):  
Michelle S. Y. Wong ◽  
Deni Taleski ◽  
Katrina A. Jolliffe
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Side Chain ◽  
Linear Peptide ◽  
Cyclic Hexapeptide ◽  
Peptide Precursors ◽  
Head To Tail Cyclization

The total synthesis of cyclic hexapeptide dichotomin A from linear peptide precursors containing penicillamine-derived pseudoproline residues is reported. The incorporation of a pseudoproline residue led to a faster reaction and higher head-to-tail cyclization yields in comparison to linear precursors containing the native valine residue. However, deprotection of the pseudoproline resulted in significant amounts of a by-product in which a threonine side chain had undergone dehydration, resulting in a low overall yield of the natural product.

scholarly journals Omniligase-1: A Powerful Tool for Peptide Head-to-Tail Cyclization

2017 ◽  
Vol 359 (12) ◽  
pp. 2050-2055 ◽  
Author(s):  
Marcel Schmidt ◽  
Ana Toplak ◽  
Peter J. L. M. Quaedflieg ◽  
Hans Ippel ◽  
Gaston J. J. Richelle ◽  
...  
Keyword(s):  
Head To Tail Cyclization

Synthesis of Nanotubule-Forming Cyclic Octapeptides via an Fmoc Strategy

1998 ◽  
Vol 51 (7) ◽  
pp. 535 ◽  
Author(s):  
Martina E. Polaskova ◽  
John N. Lambert ◽  
Nicholas J. Ede
Keyword(s):  
Aqueous Solutions ◽  
Infrared Absorption ◽  
Structural Studies ◽  
Protection Strategy ◽  
Fmoc Chemistry ◽  
Orthogonal Protection ◽  
Fmoc Strategy ◽  
Cyclic Octapeptide ◽  
Head To Tail Cyclization ◽  
Hydrogen Bonded

New syndiotactic cyclic octapeptides, namely cyclo(–D-Phe-L-Asp–D-Phe–L-Asn–D-Phe–L-Asp–D-Phe–L-Asn–) (1) and cyclo(–D-N-MeAla–L-Asp–D-N-MeAla–L-Asn–D-N-MeAla–L-Asp–D-N-MeAla–L-Asn–) (2), have been prepared, and preliminary structural studies have been conducted. The synthesis of the linear peptides was performed by using Fmoc chemistry, and head-to-tail cyclization was accomplished by using an orthogonal protection strategy and a support-bound cyclization step. Acidification of aqueous solutions of cyclic octapeptide (1) initiated formation of needlelike crystals whose morphology and infrared absorption behaviour suggested that they were hydrogen-bonded nanotubular aggregates of (1).

2-Propanephosphonic acid anhydride (T3P)-mediated segment coupling and head-to-tail cyclization of sterically hindered peptides

1999 ◽  
pp. 1847-1848 ◽  
Author(s):  
Jana Klose ◽  
Michael Bienert ◽  
Christoph Mollenkopf ◽  
Detlef Wehle ◽  
Chong-wu Zhang ◽  
...  
Keyword(s):  
Acid Anhydride ◽  
Sterically Hindered ◽  
Head To Tail Cyclization

ChemInform Abstract: Pyrrolidine and Piperidine Based Chiral Spiro and Fused Scaffolds via Build/Couple/Pair Approach.

ChemInform ◽  
2014 ◽  
Vol 45 (43) ◽  
pp. no-no
Author(s):  
Rajinikanth Mamidala ◽  
V. Surendra Babu Damerla ◽  
Rambabu Gundla ◽  
M. Thirumala Chary ◽  
Y. L. N. Murthy ◽  
...  
Keyword(s):  
Couple Pair

Build/Couple/Pair Strategy Combining the Petasis 3-Component Reaction with Ru-Catalyzed Ring-Closing Metathesis and Isomerization

2012 ◽  
Vol 14 (4) ◽  
pp. 253-257 ◽  
Author(s):  
Erhad Ascic ◽  
Sebastian T. Le Quement ◽  
Mette Ishoey ◽  
Mathilde Daugaard ◽  
Thomas E. Nielsen
Keyword(s):  
Ring Closing Metathesis ◽  
Couple Pair

Soluble Tag-Assisted Peptide Head-to-Tail Cyclization: Total Synthesis of Mahafacyclin B

2013 ◽  
Vol 15 (6) ◽  
pp. 1155-1157 ◽  
Author(s):  
Yuko Fujita ◽  
Shuji Fujita ◽  
Yohei Okada ◽  
Kazuhiro Chiba
Keyword(s):  
Total Synthesis ◽  
Head To Tail Cyclization
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