Synthesis of L-cyclic tetrapeptides by backbone amide activation CyClick strategy
Tetrahedron. 2022 Nov 5;126:133071. doi: 10.1016/j.tet.2022.133071. Epub 2022 Oct 5.ABSTRACTCyclic tetrapeptides exhibit high cellular permeability and a wide range of biological properties and thus have gained great interest in the field of medicinal chemistry. We synthesized highly strained 12-membered head to tail cyclic peptides with varying reactive amino acids, without oligomerization using the exclusively intramolecular CyClick chemistry. This occurs by a two-step process involving the low-energy formation of a 15 atom-containing cyclic imine, followed by a chemoselective ring contraction of the peptide backbone gen...
Source: Tetrahedron - November 23, 2023 Category: Chemistry Authors: Rachel Wills Victor Adebomi Caroline Spancake Ryan D Cohen Monika Raj Source Type: research
Synthesis of L-cyclic tetrapeptides by backbone amide activation CyClick strategy
Tetrahedron. 2022 Nov 5;126:133071. doi: 10.1016/j.tet.2022.133071. Epub 2022 Oct 5.ABSTRACTCyclic tetrapeptides exhibit high cellular permeability and a wide range of biological properties and thus have gained great interest in the field of medicinal chemistry. We synthesized highly strained 12-membered head to tail cyclic peptides with varying reactive amino acids, without oligomerization using the exclusively intramolecular CyClick chemistry. This occurs by a two-step process involving the low-energy formation of a 15 atom-containing cyclic imine, followed by a chemoselective ring contraction of the peptide backbone gen...
Source: Tetrahedron - November 23, 2023 Category: Chemistry Authors: Rachel Wills Victor Adebomi Caroline Spancake Ryan D Cohen Monika Raj Source Type: research
Synthesis of L-cyclic tetrapeptides by backbone amide activation CyClick strategy
Tetrahedron. 2022 Nov 5;126:133071. doi: 10.1016/j.tet.2022.133071. Epub 2022 Oct 5.ABSTRACTCyclic tetrapeptides exhibit high cellular permeability and a wide range of biological properties and thus have gained great interest in the field of medicinal chemistry. We synthesized highly strained 12-membered head to tail cyclic peptides with varying reactive amino acids, without oligomerization using the exclusively intramolecular CyClick chemistry. This occurs by a two-step process involving the low-energy formation of a 15 atom-containing cyclic imine, followed by a chemoselective ring contraction of the peptide backbone gen...
Source: Tetrahedron - November 23, 2023 Category: Chemistry Authors: Rachel Wills Victor Adebomi Caroline Spancake Ryan D Cohen Monika Raj Source Type: research
Synthesis of L-cyclic tetrapeptides by backbone amide activation CyClick strategy
Tetrahedron. 2022 Nov 5;126:133071. doi: 10.1016/j.tet.2022.133071. Epub 2022 Oct 5.ABSTRACTCyclic tetrapeptides exhibit high cellular permeability and a wide range of biological properties and thus have gained great interest in the field of medicinal chemistry. We synthesized highly strained 12-membered head to tail cyclic peptides with varying reactive amino acids, without oligomerization using the exclusively intramolecular CyClick chemistry. This occurs by a two-step process involving the low-energy formation of a 15 atom-containing cyclic imine, followed by a chemoselective ring contraction of the peptide backbone gen...
Source: Tetrahedron - November 23, 2023 Category: Chemistry Authors: Rachel Wills Victor Adebomi Caroline Spancake Ryan D Cohen Monika Raj Source Type: research
Synthesis of L-cyclic tetrapeptides by backbone amide activation CyClick strategy
Tetrahedron. 2022 Nov 5;126:133071. doi: 10.1016/j.tet.2022.133071. Epub 2022 Oct 5.ABSTRACTCyclic tetrapeptides exhibit high cellular permeability and a wide range of biological properties and thus have gained great interest in the field of medicinal chemistry. We synthesized highly strained 12-membered head to tail cyclic peptides with varying reactive amino acids, without oligomerization using the exclusively intramolecular CyClick chemistry. This occurs by a two-step process involving the low-energy formation of a 15 atom-containing cyclic imine, followed by a chemoselective ring contraction of the peptide backbone gen...
Source: Tetrahedron - November 23, 2023 Category: Chemistry Authors: Rachel Wills Victor Adebomi Caroline Spancake Ryan D Cohen Monika Raj Source Type: research
Synthesis of L-cyclic tetrapeptides by backbone amide activation CyClick strategy
Tetrahedron. 2022 Nov 5;126:133071. doi: 10.1016/j.tet.2022.133071. Epub 2022 Oct 5.ABSTRACTCyclic tetrapeptides exhibit high cellular permeability and a wide range of biological properties and thus have gained great interest in the field of medicinal chemistry. We synthesized highly strained 12-membered head to tail cyclic peptides with varying reactive amino acids, without oligomerization using the exclusively intramolecular CyClick chemistry. This occurs by a two-step process involving the low-energy formation of a 15 atom-containing cyclic imine, followed by a chemoselective ring contraction of the peptide backbone gen...
Source: Tetrahedron - November 23, 2023 Category: Chemistry Authors: Rachel Wills Victor Adebomi Caroline Spancake Ryan D Cohen Monika Raj Source Type: research
Synthesis of L-cyclic tetrapeptides by backbone amide activation CyClick strategy
Tetrahedron. 2022 Nov 5;126:133071. doi: 10.1016/j.tet.2022.133071. Epub 2022 Oct 5.ABSTRACTCyclic tetrapeptides exhibit high cellular permeability and a wide range of biological properties and thus have gained great interest in the field of medicinal chemistry. We synthesized highly strained 12-membered head to tail cyclic peptides with varying reactive amino acids, without oligomerization using the exclusively intramolecular CyClick chemistry. This occurs by a two-step process involving the low-energy formation of a 15 atom-containing cyclic imine, followed by a chemoselective ring contraction of the peptide backbone gen...
Source: Tetrahedron - November 23, 2023 Category: Chemistry Authors: Rachel Wills Victor Adebomi Caroline Spancake Ryan D Cohen Monika Raj Source Type: research
Synthesis of L-cyclic tetrapeptides by backbone amide activation CyClick strategy
Tetrahedron. 2022 Nov 5;126:133071. doi: 10.1016/j.tet.2022.133071. Epub 2022 Oct 5.ABSTRACTCyclic tetrapeptides exhibit high cellular permeability and a wide range of biological properties and thus have gained great interest in the field of medicinal chemistry. We synthesized highly strained 12-membered head to tail cyclic peptides with varying reactive amino acids, without oligomerization using the exclusively intramolecular CyClick chemistry. This occurs by a two-step process involving the low-energy formation of a 15 atom-containing cyclic imine, followed by a chemoselective ring contraction of the peptide backbone gen...
Source: Tetrahedron - November 23, 2023 Category: Chemistry Authors: Rachel Wills Victor Adebomi Caroline Spancake Ryan D Cohen Monika Raj Source Type: research
Synthesis of L-cyclic tetrapeptides by backbone amide activation CyClick strategy
Tetrahedron. 2022 Nov 5;126:133071. doi: 10.1016/j.tet.2022.133071. Epub 2022 Oct 5.ABSTRACTCyclic tetrapeptides exhibit high cellular permeability and a wide range of biological properties and thus have gained great interest in the field of medicinal chemistry. We synthesized highly strained 12-membered head to tail cyclic peptides with varying reactive amino acids, without oligomerization using the exclusively intramolecular CyClick chemistry. This occurs by a two-step process involving the low-energy formation of a 15 atom-containing cyclic imine, followed by a chemoselective ring contraction of the peptide backbone gen...
Source: Tetrahedron - November 23, 2023 Category: Chemistry Authors: Rachel Wills Victor Adebomi Caroline Spancake Ryan D Cohen Monika Raj Source Type: research
Chemoenzymatic Synthesis of < em > N < /em > -Acetyl Analogues of 9- < em > O < /em > -Acetylated b-Series Gangliosides
Tetrahedron. 2023 Aug 3;142:133522. doi: 10.1016/j.tet.2023.133522. Epub 2023 Jun 15.ABSTRACTThe stable N-acetyl analogues of biologically important 9-O-acetylated b-series gangliosides including 9NAc-GD3, 9NAc-GD2, 9NAc-GD1b, and 9NAc-GT1b were chemoenzymatically synthesized from a GM3 sphingosine. Two chemoenzymatic methods using either 6-azido-6-deoxy-N-acetylmannosamine (ManNAc6N3) as a chemoenzymatic synthon or 6-acetamido-6-deoxy-N-acetylmannosamine (ManNAc6NAc) as an enzymatic precursor for 9-acetamido-9-deoxy-N-acetylneuraminic acid (Neu5Ac9NAc) were developed and compared for the synthesis of 9NAc-GD3. The latter ...
Source: Tetrahedron - November 20, 2023 Category: Chemistry Authors: Hai Yu Zimin Zheng Libo Zhang Xiaohong Yang Ajit Varki Xi Chen Source Type: research
Chemoenzymatic Synthesis of < em > N < /em > -Acetyl Analogues of 9- < em > O < /em > -Acetylated b-Series Gangliosides
Tetrahedron. 2023 Aug 3;142:133522. doi: 10.1016/j.tet.2023.133522. Epub 2023 Jun 15.ABSTRACTThe stable N-acetyl analogues of biologically important 9-O-acetylated b-series gangliosides including 9NAc-GD3, 9NAc-GD2, 9NAc-GD1b, and 9NAc-GT1b were chemoenzymatically synthesized from a GM3 sphingosine. Two chemoenzymatic methods using either 6-azido-6-deoxy-N-acetylmannosamine (ManNAc6N3) as a chemoenzymatic synthon or 6-acetamido-6-deoxy-N-acetylmannosamine (ManNAc6NAc) as an enzymatic precursor for 9-acetamido-9-deoxy-N-acetylneuraminic acid (Neu5Ac9NAc) were developed and compared for the synthesis of 9NAc-GD3. The latter ...
Source: Tetrahedron - November 20, 2023 Category: Chemistry Authors: Hai Yu Zimin Zheng Libo Zhang Xiaohong Yang Ajit Varki Xi Chen Source Type: research
Ring-Opening Reactions of Phosphoramidate Heterocycles
We present protocols for the conversion of phosphoramidate heterocycles into 1,3-chloroamines and 1,3-aminoalcohols. For the formation of chloroamines, our optimized protocol involves heating the phosphoramidate starting material with 4 equivalents of HCl in a dioxane/toluene solvent mixture. The substituents on the phosphoramidate starting material have a profound influence on product formation. Phosphoramidates with a variety of aza-heterocyclic substituents engage, but those containing a 5-chloro-8-quinolinol arm are most competent for 1,3-chloroamine formation. Furthermore, only the phosphoramidate cis diastereomers al...
Source: Tetrahedron - October 27, 2023 Category: Chemistry Authors: Annu Anna Thomas Frederick J Seidl Joel T Mague Shyam Sathyamoorthi Source Type: research
Ring-Opening Reactions of Phosphoramidate Heterocycles
We present protocols for the conversion of phosphoramidate heterocycles into 1,3-chloroamines and 1,3-aminoalcohols. For the formation of chloroamines, our optimized protocol involves heating the phosphoramidate starting material with 4 equivalents of HCl in a dioxane/toluene solvent mixture. The substituents on the phosphoramidate starting material have a profound influence on product formation. Phosphoramidates with a variety of aza-heterocyclic substituents engage, but those containing a 5-chloro-8-quinolinol arm are most competent for 1,3-chloroamine formation. Furthermore, only the phosphoramidate cis diastereomers al...
Source: Tetrahedron - October 27, 2023 Category: Chemistry Authors: Annu Anna Thomas Frederick J Seidl Joel T Mague Shyam Sathyamoorthi Source Type: research
Ring-Opening Reactions of Phosphoramidate Heterocycles
We present protocols for the conversion of phosphoramidate heterocycles into 1,3-chloroamines and 1,3-aminoalcohols. For the formation of chloroamines, our optimized protocol involves heating the phosphoramidate starting material with 4 equivalents of HCl in a dioxane/toluene solvent mixture. The substituents on the phosphoramidate starting material have a profound influence on product formation. Phosphoramidates with a variety of aza-heterocyclic substituents engage, but those containing a 5-chloro-8-quinolinol arm are most competent for 1,3-chloroamine formation. Furthermore, only the phosphoramidate cis diastereomers al...
Source: Tetrahedron - October 27, 2023 Category: Chemistry Authors: Annu Anna Thomas Frederick J Seidl Joel T Mague Shyam Sathyamoorthi Source Type: research
Ring-Opening Reactions of Phosphoramidate Heterocycles
We present protocols for the conversion of phosphoramidate heterocycles into 1,3-chloroamines and 1,3-aminoalcohols. For the formation of chloroamines, our optimized protocol involves heating the phosphoramidate starting material with 4 equivalents of HCl in a dioxane/toluene solvent mixture. The substituents on the phosphoramidate starting material have a profound influence on product formation. Phosphoramidates with a variety of aza-heterocyclic substituents engage, but those containing a 5-chloro-8-quinolinol arm are most competent for 1,3-chloroamine formation. Furthermore, only the phosphoramidate cis diastereomers al...
Source: Tetrahedron - October 27, 2023 Category: Chemistry Authors: Annu Anna Thomas Frederick J Seidl Joel T Mague Shyam Sathyamoorthi Source Type: research
