Palladium mediated deallylation in fully aqueous conditions for native chemical ligation at aspartic and glutamic acid sites

2018 ◽  
Vol 16 (22) ◽  
pp. 4061-4064 ◽  
Author(s):  
Muhammad Jbara ◽  
Emad Eid ◽  
Ashraf Brik
Keyword(s):  
Glutamic Acid ◽  
Acid Sites ◽  
Native Chemical Ligation ◽  
Side Chain ◽  
Chemical Ligation ◽  
Peptide Thioester ◽  
Aqueous Conditions

An efficient native chemical ligation approach at Asp and Glu sites is reported applying a hydrazide precursor, as a peptide thioester, and allyl protection at the side chain of Asp and Glu.

scholarly journals Investigation of Cysteine as an Activator of Side-Chain N→S Acyl Transfer and Tail-to-Side-Chain Cyclization

Synlett ◽  
2017 ◽  
Vol 28 (15) ◽  
pp. 1923-1928 ◽  
Author(s):  
Derek Macmillan ◽  
Durbis Castillo-Pazos
Keyword(s):  
Glutamic Acid ◽  
Chain Length ◽  
Cyclic Peptides ◽  
Fine Tuning ◽  
Acyl Transfer ◽  
Native Chemical Ligation ◽  
Side Chain ◽  
Chemical Ligation ◽  
Popular Method ◽  
Slow Reaction

N→S Acyl transfer is a popular method for the postsynthesis production of peptide C α-thioesters for use in native chemical ligation and for the synthesis of head-to-tail cyclic peptides. Meanwhile thioester formation at the side chain of aspartic or glutamic acids, leading to tail-to-side-chain-cyclized species, is less common. Herein we explore the potential for cysteine to function as a latent thioester when appended to the side chain of glutamic acid. Initial insights gained through study of C-terminal β-alanine as a model for the increased chain length were ultimately applied to peptide macrocyclization. Our results emphasize the increased barrier to acyl transfer at the glutamic acid side chain and indicate how a slow reaction, facilitated by cysteine itself, may be accelerated by fine-tuning of the stereoelectronic environment.

Synthesis of misfolded glycoprotein dimers through native chemical ligation of a dimeric peptide thioester

2016 ◽  
Vol 14 (25) ◽  
pp. 6088-6094 ◽  
Author(s):  
Masayuki Izumi ◽  
Shinji Komaki ◽  
Ryo Okamoto ◽  
Akira Seko ◽  
Yoichi Takeda ◽  
...  
Keyword(s):  
Native Chemical Ligation ◽  
Chemical Ligation ◽  
Peptide Thioester

Misfolded glycoprotein dimers were synthesized through double native chemical ligation between a dimeric peptide-α-thioester, glycopeptide, and non-glycosylated peptide.

scholarly journals Serine promoted synthesis of peptide thioester-precursor on solid support for native chemical ligation

2017 ◽  
Vol 8 (1) ◽  
pp. 117-123 ◽  
Author(s):  
Hader E. Elashal ◽  
Yonnette E. Sim ◽  
Monika Raj
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Solid Support ◽  
Native Chemical Ligation ◽  
Selective Activation ◽  
Chemical Ligation ◽  
Peptide Thioester ◽  
Peptide Thioesters

Fmoc solid phase peptide synthesis of peptide thioesters by displacement of the cyclic urethane moiety obtained by the selective activation of C-terminal serine.

scholarly journals Side-Chain Cysteine-Functionalized Poly(2-oxazoline)s for Multiple Peptide Conjugation by Native Chemical Ligation

2015 ◽  
Vol 16 (4) ◽  
pp. 1088-1094 ◽  
Author(s):  
Michael Schmitz ◽  
Matthias Kuhlmann ◽  
Oliver Reimann ◽  
Christian P. R. Hackenberger ◽  
Jürgen Groll
Keyword(s):  
Native Chemical Ligation ◽  
Side Chain ◽  
Chemical Ligation ◽  
Peptide Conjugation

Poly(glutamic acid) hydrogels crosslinked via native chemical ligation

2017 ◽  
Vol 41 (16) ◽  
pp. 8656-8662 ◽  
Author(s):  
Zhiping Fan ◽  
Ping Cheng ◽  
Min Liu ◽  
Dacheng Li ◽  
Guiqin Liu ◽  
...  
Keyword(s):  
Glutamic Acid ◽  
Native Chemical Ligation ◽  
Chemical Ligation ◽  
Tunable Properties ◽  
Good Biocompatibility

Poly(glutamic acid) hydrogels crosslinked by NCL have good biocompatibility and tunable properties.

scholarly journals A straightforward method for automated Fmoc-based synthesis of bio-inspired peptide crypto-thioesters

2016 ◽  
Vol 7 (1) ◽  
pp. 339-345 ◽  
Author(s):  
Victor P. Terrier ◽  
Hélène Adihou ◽  
Mathieu Arnould ◽  
Agnès F. Delmas ◽  
Vincent Aucagne
Keyword(s):  
Native Chemical Ligation ◽  
Chemical Ligation ◽  
Straightforward Method ◽  
Peptide Thioester

A bio-inspired method for the synthesis of peptide thioester surrogates for native chemical ligation was developed. The process can be fully automated and does not require postsynthetic steps.

Hybrid polypeptide hydrogels produced via native chemical ligation

RSC Advances ◽  
2015 ◽  
Vol 5 (22) ◽  
pp. 16740-16747 ◽  
Author(s):  
Zhiping Fan ◽  
Yemin Zhang ◽  
Jinkai Ji ◽  
Xinsong Li
Keyword(s):  
Glutamic Acid ◽  
Native Chemical Ligation ◽  
Chemical Ligation ◽  
Tunable Properties ◽  
Hybrid Hydrogels ◽  
Good Biocompatibility

The NCL crosslinked hybrid hydrogels composed of poly(γ-glutamic acid) and ε-poly-lysine have good biocompatibility and tunable properties.

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