Biocompatible synthesis of macrocyclic thiazole peptides from chiral α-amino nitriles

Minghao Shang; Junming He; Michael G. Gardiner; Christoph Nitsche

doi:10.1039/d4ob01989j

Biocompatible synthesis of macrocyclic thiazole peptides from chiral α-amino nitriles

Minghao Shang, Junming He, Michael G. Gardiner, Christoph Nitsche

The Australian National University

Research output: Contribution to journal › Comment/debate › peer-review

Abstract

Macrocyclic peptides containing a thiazole heterocycle exhibit fascinating properties in natural products and future therapeutics. We report a biocompatible macrocyclisation approach facilitated by an N-terminal cysteine and C-terminal nitriles. The use of various chiral alpha-amino nitriles enables the incorporation of diverse hydrophobic side chains adjacent to the thiazole motif.

Original language	English
Number of pages	4
Journal	Organic and Biomolecular Chemistry
Early online date	Dec 2024
DOIs	https://doi.org/10.1039/d4ob01989j
Publication status	Published - 30 Dec 2024

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title = "Biocompatible synthesis of macrocyclic thiazole peptides from chiral α-amino nitriles",

abstract = "Macrocyclic peptides containing a thiazole heterocycle exhibit fascinating properties in natural products and future therapeutics. We report a biocompatible macrocyclisation approach facilitated by an N-terminal cysteine and C-terminal nitriles. The use of various chiral alpha-amino nitriles enables the incorporation of diverse hydrophobic side chains adjacent to the thiazole motif.",

keywords = "Cyclic peptide, Hexapeptides",

author = "Minghao Shang and Junming He and Gardiner, {Michael G.} and Christoph Nitsche",

year = "2024",

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T1 - Biocompatible synthesis of macrocyclic thiazole peptides from chiral α-amino nitriles

AU - Shang, Minghao

AU - He, Junming

AU - Gardiner, Michael G.

AU - Nitsche, Christoph

PY - 2024/12/30

Y1 - 2024/12/30

N2 - Macrocyclic peptides containing a thiazole heterocycle exhibit fascinating properties in natural products and future therapeutics. We report a biocompatible macrocyclisation approach facilitated by an N-terminal cysteine and C-terminal nitriles. The use of various chiral alpha-amino nitriles enables the incorporation of diverse hydrophobic side chains adjacent to the thiazole motif.

AB - Macrocyclic peptides containing a thiazole heterocycle exhibit fascinating properties in natural products and future therapeutics. We report a biocompatible macrocyclisation approach facilitated by an N-terminal cysteine and C-terminal nitriles. The use of various chiral alpha-amino nitriles enables the incorporation of diverse hydrophobic side chains adjacent to the thiazole motif.

KW - Cyclic peptide

KW - Hexapeptides

UR - https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=anu_research_portal_plus2&SrcAuth=WosAPI&KeyUT=WOS:001390652000001&DestLinkType=FullRecord&DestApp=WOS_CPL

U2 - 10.1039/d4ob01989j

DO - 10.1039/d4ob01989j

M3 - Comment/debate

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SN - 1477-0520

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

ER -

Biocompatible synthesis of macrocyclic thiazole peptides from chiral α-amino nitriles

Abstract

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