scholarly journals Solid-Phase Total Synthesis of Dehydrotryptophan-Bearing Cyclic Peptides Tunicyclin B, Sclerotide A, CDA3a, and CDA4a using a Protected β-Hydroxytryptophan Building Block

2021 ◽  
Author(s):  
Matthew Diamandas ◽  
Ryan Moreira ◽  
Scott D. Taylor
Keyword(s):  
Total Synthesis ◽  
Building Block ◽  
Cyclic Peptides ◽  
Solid Phase

scholarly journals Efficient and Reproducible Synthesis of an Fmoc-protected Tn Antigen

2021 ◽  
Author(s):  
Michael R. Reynolds ◽  
Sabrina Piazza ◽  
Jonathan Chiaramonte ◽  
Fabiola A. Chapa-Villarreal ◽  
John Trant
Keyword(s):  
Total Synthesis ◽  
Peptide Synthesis ◽  
Building Block ◽  
Large Scale ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Tn Antigen ◽  
Palladium Catalyzed ◽  
Glycosyl Donor ◽  
Antigen A

The total synthesis of the Thomsen-nouveau (Tn) antigen, a tumour-associated O-linked mucin glycopeptide, was achieved through a concise route. The key glycosylation step proved challenging to reproduce from the literature precedents and was most reliably accomplished using a palladium-catalyzed coupling between the glycosyl donor and Fmoc-functionalized serine acceptor to form the target in moderate yields. This is, to the best of our knowledge, the shortest synthesis reported from galactose for preparing this essential building block for large-scale solid phase peptide synthesis.

scholarly journals Efficient and Reproducible Synthesis of an Fmoc-protected Tn Antigen

2021 ◽  
Author(s):  
Michael R. Reynolds ◽  
Sabrina Piazza ◽  
Jonathan Chiaramonte ◽  
Fabiola A. Chapa-Villarreal ◽  
John Trant
Keyword(s):  
Total Synthesis ◽  
Peptide Synthesis ◽  
Building Block ◽  
Large Scale ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Tn Antigen ◽  
Palladium Catalyzed ◽  
Glycosyl Donor ◽  
Antigen A

The total synthesis of the Thomsen-nouveau (Tn) antigen, a tumour-associated O-linked mucin glycopeptide, was achieved through a concise route. The key glycosylation step proved challenging to reproduce from the literature precedents and was most reliably accomplished using a palladium-catalyzed coupling between the glycosyl donor and Fmoc-functionalized serine acceptor to form the target in moderate yields. This is, to the best of our knowledge, the shortest synthesis reported from galactose for preparing this essential building block for large-scale solid phase peptide synthesis.

scholarly journals Solid-phase synthesis of biaryl cyclic peptides containing a histidine-tyrosine linkage

Tetrahedron ◽  
2019 ◽  
Vol 75 (18) ◽  
pp. 2625-2636 ◽  
Author(s):  
Iteng Ng-Choi ◽  
Àngel Oliveras ◽  
Marta Planas ◽  
Lidia Feliu
Keyword(s):  
Cyclic Peptides ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis

scholarly journals Total synthesis of biselide A

2021 ◽  
Author(s):  
Venugopal Rao Challa ◽  
Daniel Kwon ◽  
Matthew Taron ◽  
Hope Fan ◽  
Baldip Kang ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Building Block ◽  
Chiral Building Block

A total synthesis of the marine macrolide biselide A is described that relies on an enantiomerically enriched α-chloroaldehyde as the sole chiral building block.

scholarly journals Automated solid-phase synthesis of oligosaccharides containing sialic acids

2015 ◽  
Vol 11 ◽  
pp. 617-621 ◽  
Author(s):  
Chian-Hui Lai ◽  
Heung Sik Hahm ◽  
Chien-Fu Liang ◽  
Peter H Seeberger
Keyword(s):  
Sialic Acid ◽  
Building Block ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Sialic Acids ◽  
Phase Synthesis ◽  
Glycosyl Phosphate

A sialic acid glycosyl phosphate building block was designed and synthesized. This building block was used to prepare α-sialylated oligosaccharides by automated solid-phase synthesis selectively.

A novel, convenient, three-dimensional orthogonal strategy for solid-phase synthesis of cyclic peptides

1993 ◽  
Vol 34 (10) ◽  
pp. 1549-1552 ◽  
Author(s):  
Steven A. Kates ◽  
Nuria A. Solé ◽  
Charles R. Johnson ◽  
Derek Hudson ◽  
George Barany ◽  
...  
Keyword(s):  
Cyclic Peptides ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Three Dimensional ◽  
Phase Synthesis

scholarly journals Regiodivergent Biocatalytic Hydroxylation of L-Glutamine Facilitated by Characterization of Non-Heme Dioxygenases from Non-Ribosomal Peptide Biosyntheses

2021 ◽  
Author(s):  
Hans Renata ◽  
Emily Shimizu ◽  
Christian Zwick
Keyword(s):  
Amino Acid ◽  
Building Block ◽  
Solid Phase ◽  
Functional Characterization ◽  
Free Standing ◽  
Substrate Specificities ◽  
Total Turnover

We report the functional characterization of two iron- and a-ketoglutarate-dependent dioxygenases that are capable of hydroxylating free-standing glutamine at its C3 and C4 position respectively. In particular, the C4 hydroxylase, Q4Ox, catalyzes the reaction with approximately 4,300 total turnover numbers, facilitating synthesis of a solid-phase compatible building block and stereochemical elucidation at the C4 position of the hydroxylated product. This work will enable the development of novel synthetic strategies to prepare useful glutamine derivatives and stimulate further discoveries of new amino acid hydroxylases with distinct substrate specificities.<br>

scholarly journals Regiodivergent Biocatalytic Hydroxylation of L-Glutamine Facilitated by Characterization of Non-Heme Dioxygenases from Non-Ribosomal Peptide Biosyntheses

2021 ◽  
Author(s):  
Hans Renata ◽  
Emily Shimizu ◽  
Christian Zwick
Keyword(s):  
Amino Acid ◽  
Building Block ◽  
Solid Phase ◽  
Functional Characterization ◽  
Free Standing ◽  
Substrate Specificities ◽  
Total Turnover

We report the functional characterization of two iron- and a-ketoglutarate-dependent dioxygenases that are capable of hydroxylating free-standing glutamine at its C3 and C4 position respectively. In particular, the C4 hydroxylase, Q4Ox, catalyzes the reaction with approximately 4,300 total turnover numbers, facilitating synthesis of a solid-phase compatible building block and stereochemical elucidation at the C4 position of the hydroxylated product. This work will enable the development of novel synthetic strategies to prepare useful glutamine derivatives and stimulate further discoveries of new amino acid hydroxylases with distinct substrate specificities.<br>

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