ge-2270-a and pyridine

ge-2270-a has been researched along with pyridine* in 2 studies

Other Studies

2 other study(ies) available for ge-2270-a and pyridine

Article	Year
Capturing linear intermediates and C-terminal variants during maturation of the thiopeptide GE2270. Chemistry & biology, 2013, Aug-22, Volume: 20, Issue:8 Thiopeptides are ribosomally synthesized, posttranslationally modified peptides with potent activity against Gram-positives. However, only GE2270 has yielded semisynthetic derivatives under clinical investigations. The pbt gene cluster from the GE2270 producer Planobispora rosea was successfully expressed in the genetically tractable Nonomuraea ATCC39727. Gene deletions established that PbtO, PbtM1, PbtM2, PbtM3, and PbtM4 are involved in regiospecific hydroxylation and methylations of GE2270, leading to the generation of various derivatives with altered decorations. Further deletions established that PbtH and PbtG1 are involved in C-terminal amide and oxazoline formation, respectively. Surprisingly, preventing either step resulted in the accumulation of linear precursors in which the pyridine-generated macrocycle failed to form, and only one of the pyridine-forming serine residues had been dehydrated. Often, these linear precursors present a shortened C terminus but retain the full set of methylation and hydroxylation decorations. Topics: Actinomycetales; Amino Acid Sequence; Anti-Bacterial Agents; Genes, Fungal; Molecular Sequence Data; Multigene Family; Oxazoles; Peptides, Cyclic; Pyridines; Thiazoles	2013
Total synthesis of thiopeptide antibiotics GE2270A, GE2270T, and GE2270C1. Chemistry, an Asian journal, 2008, Feb-01, Volume: 3, Issue:2 The total syntheses of the thiopeptide antibiotics GE2270A (7), GE2270T (8), and GE2270C1 (9) are described. The original synthetic strategies employed utilized the hetero-Diels-Alder reaction to construct the pyridine core of the target molecules and relied on a macrolactamization process to construct the macrocycle. The hetero-Diels-Alder-based strategy finally evolved allows the introduction of all four thiazole units attached to the pyridine ring and a one-pot sequence for macrocyclization and side-chain extension, culminating in highly convergent and expedient syntheses of these molecules as exemplified by a 24-step synthesis of GE2270C1 (9). Topics: Acetamides; Anti-Bacterial Agents; Azoles; Hydroxylation; Macrolides; Molecular Structure; Peptides, Cyclic; Phenylalanine; Pyridines; Sulfhydryl Compounds; Thiazoles	2008

Article

Year

Capturing linear intermediates and C-terminal variants during maturation of the thiopeptide GE2270.

Chemistry & biology, 2013, Aug-22, Volume: 20, Issue:8

Thiopeptides are ribosomally synthesized, posttranslationally modified peptides with potent activity against Gram-positives. However, only GE2270 has yielded semisynthetic derivatives under clinical investigations. The pbt gene cluster from the GE2270 producer Planobispora rosea was successfully expressed in the genetically tractable Nonomuraea ATCC39727. Gene deletions established that PbtO, PbtM1, PbtM2, PbtM3, and PbtM4 are involved in regiospecific hydroxylation and methylations of GE2270, leading to the generation of various derivatives with altered decorations. Further deletions established that PbtH and PbtG1 are involved in C-terminal amide and oxazoline formation, respectively. Surprisingly, preventing either step resulted in the accumulation of linear precursors in which the pyridine-generated macrocycle failed to form, and only one of the pyridine-forming serine residues had been dehydrated. Often, these linear precursors present a shortened C terminus but retain the full set of methylation and hydroxylation decorations.

Topics: Actinomycetales; Amino Acid Sequence; Anti-Bacterial Agents; Genes, Fungal; Molecular Sequence Data; Multigene Family; Oxazoles; Peptides, Cyclic; Pyridines; Thiazoles

2013

Total synthesis of thiopeptide antibiotics GE2270A, GE2270T, and GE2270C1.

Chemistry, an Asian journal, 2008, Feb-01, Volume: 3, Issue:2

The total syntheses of the thiopeptide antibiotics GE2270A (7), GE2270T (8), and GE2270C1 (9) are described. The original synthetic strategies employed utilized the hetero-Diels-Alder reaction to construct the pyridine core of the target molecules and relied on a macrolactamization process to construct the macrocycle. The hetero-Diels-Alder-based strategy finally evolved allows the introduction of all four thiazole units attached to the pyridine ring and a one-pot sequence for macrocyclization and side-chain extension, culminating in highly convergent and expedient syntheses of these molecules as exemplified by a 24-step synthesis of GE2270C1 (9).

Topics: Acetamides; Anti-Bacterial Agents; Azoles; Hydroxylation; Macrolides; Molecular Structure; Peptides, Cyclic; Phenylalanine; Pyridines; Sulfhydryl Compounds; Thiazoles

2008