Synthesis of 4- < em > O < /em > -(4-Amino-4-deoxy- β-D-xylopyranosyl)paromomycin and 4- < em > S < /em > -( β-D-Xylopyranosyl)-4-deoxy-4'-thio-paromomycin and Evaluation of their Antiribosomal and Antibacterial Activity
Tetrahedron. 2023 Apr 6;135:133330. doi: 10.1016/j.tet.2023.133330. Epub 2023 Feb 23.ABSTRACTThe design, synthesis and antiribosomal and antibacterial activity of two novel glycosides of the aminoglycoside antibiotic paromomycin are described. The first carries of 4-amino-4-deoxy-β-D-xylopyranosyl moiety at the paromomycin 4'-position and is approximately two-fold more active than the corresponding β-D-xylopyranosyl derivative. The second is a 4'-(β-D-xylopyranosylthio) derivative of 4'-deoxyparomomycin that is unexpectedly less active than the simple β-D-xylopyranosyl derivative, perhaps because of the insertion of th...
Source: Tetrahedron - April 10, 2023 Category: Chemistry Authors: Rukshana Mohamad-Ramshan Chennaiah Ande Takahiko Matsushita Klara Haldimann Andrea Vasella Sven N Hobbie David Crich Source Type: research
The Analysis of Two Distinct Strategies toward the Enantioselective Formal Total Synthesis of (+)-Gelsenicine
Tetrahedron. 2023 Mar 21;134:133278. doi: 10.1016/j.tet.2023.133278. Epub 2023 Jan 21.ABSTRACTA full account of a formal enantioselective total synthesis of (+)-gelsenicine is described. Separate strategies based on catalytic cycloisomerization as the central step are considered. One plan involves chirality transfer from enantioenriched substrates, while the other employs asymmetric catalysis. The chirality transfer strategy is less effective, while in the latter, phosphoramidite- and bisphosphine-gold complexes are tested and ultimately provide a key intermediate in high enantiopurity in our Gelsemium alkaloid syntheses.P...
Source: Tetrahedron - April 10, 2023 Category: Chemistry Authors: Haofan Ji Phil C Knutson Christopher M Harrington Yan-Ting Ke Eric M Ferreira Source Type: research
Synthesis of 4- < em > O < /em > -(4-Amino-4-deoxy- β-D-xylopyranosyl)paromomycin and 4- < em > S < /em > -( β-D-Xylopyranosyl)-4-deoxy-4'-thio-paromomycin and Evaluation of their Antiribosomal and Antibacterial Activity
Tetrahedron. 2023 Apr 6;135:133330. doi: 10.1016/j.tet.2023.133330. Epub 2023 Feb 23.ABSTRACTThe design, synthesis and antiribosomal and antibacterial activity of two novel glycosides of the aminoglycoside antibiotic paromomycin are described. The first carries of 4-amino-4-deoxy-β-D-xylopyranosyl moiety at the paromomycin 4'-position and is approximately two-fold more active than the corresponding β-D-xylopyranosyl derivative. The second is a 4'-(β-D-xylopyranosylthio) derivative of 4'-deoxyparomomycin that is unexpectedly less active than the simple β-D-xylopyranosyl derivative, perhaps because of the insertion of th...
Source: Tetrahedron - April 10, 2023 Category: Chemistry Authors: Rukshana Mohamad-Ramshan Chennaiah Ande Takahiko Matsushita Klara Haldimann Andrea Vasella Sven N Hobbie David Crich Source Type: research
The Analysis of Two Distinct Strategies toward the Enantioselective Formal Total Synthesis of (+)-Gelsenicine
Tetrahedron. 2023 Mar 21;134:133278. doi: 10.1016/j.tet.2023.133278. Epub 2023 Jan 21.ABSTRACTA full account of a formal enantioselective total synthesis of (+)-gelsenicine is described. Separate strategies based on catalytic cycloisomerization as the central step are considered. One plan involves chirality transfer from enantioenriched substrates, while the other employs asymmetric catalysis. The chirality transfer strategy is less effective, while in the latter, phosphoramidite- and bisphosphine-gold complexes are tested and ultimately provide a key intermediate in high enantiopurity in our Gelsemium alkaloid syntheses.P...
Source: Tetrahedron - April 10, 2023 Category: Chemistry Authors: Haofan Ji Phil C Knutson Christopher M Harrington Yan-Ting Ke Eric M Ferreira Source Type: research
Synthesis of 4- < em > O < /em > -(4-Amino-4-deoxy- β-D-xylopyranosyl)paromomycin and 4- < em > S < /em > -( β-D-Xylopyranosyl)-4-deoxy-4'-thio-paromomycin and Evaluation of their Antiribosomal and Antibacterial Activity
Tetrahedron. 2023 Apr 6;135:133330. doi: 10.1016/j.tet.2023.133330. Epub 2023 Feb 23.ABSTRACTThe design, synthesis and antiribosomal and antibacterial activity of two novel glycosides of the aminoglycoside antibiotic paromomycin are described. The first carries of 4-amino-4-deoxy-β-D-xylopyranosyl moiety at the paromomycin 4'-position and is approximately two-fold more active than the corresponding β-D-xylopyranosyl derivative. The second is a 4'-(β-D-xylopyranosylthio) derivative of 4'-deoxyparomomycin that is unexpectedly less active than the simple β-D-xylopyranosyl derivative, perhaps because of the insertion of th...
Source: Tetrahedron - April 10, 2023 Category: Chemistry Authors: Rukshana Mohamad-Ramshan Chennaiah Ande Takahiko Matsushita Klara Haldimann Andrea Vasella Sven N Hobbie David Crich Source Type: research
The Analysis of Two Distinct Strategies toward the Enantioselective Formal Total Synthesis of (+)-Gelsenicine
Tetrahedron. 2023 Mar 21;134:133278. doi: 10.1016/j.tet.2023.133278. Epub 2023 Jan 21.ABSTRACTA full account of a formal enantioselective total synthesis of (+)-gelsenicine is described. Separate strategies based on catalytic cycloisomerization as the central step are considered. One plan involves chirality transfer from enantioenriched substrates, while the other employs asymmetric catalysis. The chirality transfer strategy is less effective, while in the latter, phosphoramidite- and bisphosphine-gold complexes are tested and ultimately provide a key intermediate in high enantiopurity in our Gelsemium alkaloid syntheses.P...
Source: Tetrahedron - April 10, 2023 Category: Chemistry Authors: Haofan Ji Phil C Knutson Christopher M Harrington Yan-Ting Ke Eric M Ferreira Source Type: research
Synthesis of 4- < em > O < /em > -(4-Amino-4-deoxy- β-D-xylopyranosyl)paromomycin and 4- < em > S < /em > -( β-D-Xylopyranosyl)-4-deoxy-4'-thio-paromomycin and Evaluation of their Antiribosomal and Antibacterial Activity
Tetrahedron. 2023 Apr 6;135:133330. doi: 10.1016/j.tet.2023.133330. Epub 2023 Feb 23.ABSTRACTThe design, synthesis and antiribosomal and antibacterial activity of two novel glycosides of the aminoglycoside antibiotic paromomycin are described. The first carries of 4-amino-4-deoxy-β-D-xylopyranosyl moiety at the paromomycin 4'-position and is approximately two-fold more active than the corresponding β-D-xylopyranosyl derivative. The second is a 4'-(β-D-xylopyranosylthio) derivative of 4'-deoxyparomomycin that is unexpectedly less active than the simple β-D-xylopyranosyl derivative, perhaps because of the insertion of th...
Source: Tetrahedron - April 10, 2023 Category: Chemistry Authors: Rukshana Mohamad-Ramshan Chennaiah Ande Takahiko Matsushita Klara Haldimann Andrea Vasella Sven N Hobbie David Crich Source Type: research
The Analysis of Two Distinct Strategies toward the Enantioselective Formal Total Synthesis of (+)-Gelsenicine
Tetrahedron. 2023 Mar 21;134:133278. doi: 10.1016/j.tet.2023.133278. Epub 2023 Jan 21.ABSTRACTA full account of a formal enantioselective total synthesis of (+)-gelsenicine is described. Separate strategies based on catalytic cycloisomerization as the central step are considered. One plan involves chirality transfer from enantioenriched substrates, while the other employs asymmetric catalysis. The chirality transfer strategy is less effective, while in the latter, phosphoramidite- and bisphosphine-gold complexes are tested and ultimately provide a key intermediate in high enantiopurity in our Gelsemium alkaloid syntheses.P...
Source: Tetrahedron - April 10, 2023 Category: Chemistry Authors: Haofan Ji Phil C Knutson Christopher M Harrington Yan-Ting Ke Eric M Ferreira Source Type: research
Synthesis of 4- < em > O < /em > -(4-Amino-4-deoxy- β-D-xylopyranosyl)paromomycin and 4- < em > S < /em > -( β-D-Xylopyranosyl)-4-deoxy-4'-thio-paromomycin and Evaluation of their Antiribosomal and Antibacterial Activity
Tetrahedron. 2023 Apr 6;135:133330. doi: 10.1016/j.tet.2023.133330. Epub 2023 Feb 23.ABSTRACTThe design, synthesis and antiribosomal and antibacterial activity of two novel glycosides of the aminoglycoside antibiotic paromomycin are described. The first carries of 4-amino-4-deoxy-β-D-xylopyranosyl moiety at the paromomycin 4'-position and is approximately two-fold more active than the corresponding β-D-xylopyranosyl derivative. The second is a 4'-(β-D-xylopyranosylthio) derivative of 4'-deoxyparomomycin that is unexpectedly less active than the simple β-D-xylopyranosyl derivative, perhaps because of the insertion of th...
Source: Tetrahedron - April 10, 2023 Category: Chemistry Authors: Rukshana Mohamad-Ramshan Chennaiah Ande Takahiko Matsushita Klara Haldimann Andrea Vasella Sven N Hobbie David Crich Source Type: research
The Analysis of Two Distinct Strategies toward the Enantioselective Formal Total Synthesis of (+)-Gelsenicine
Tetrahedron. 2023 Mar 21;134:133278. doi: 10.1016/j.tet.2023.133278. Epub 2023 Jan 21.ABSTRACTA full account of a formal enantioselective total synthesis of (+)-gelsenicine is described. Separate strategies based on catalytic cycloisomerization as the central step are considered. One plan involves chirality transfer from enantioenriched substrates, while the other employs asymmetric catalysis. The chirality transfer strategy is less effective, while in the latter, phosphoramidite- and bisphosphine-gold complexes are tested and ultimately provide a key intermediate in high enantiopurity in our Gelsemium alkaloid syntheses.P...
Source: Tetrahedron - April 10, 2023 Category: Chemistry Authors: Haofan Ji Phil C Knutson Christopher M Harrington Yan-Ting Ke Eric M Ferreira Source Type: research
Synthesis of 4- < em > O < /em > -(4-Amino-4-deoxy- β-D-xylopyranosyl)paromomycin and 4- < em > S < /em > -( β-D-Xylopyranosyl)-4-deoxy-4'-thio-paromomycin and Evaluation of their Antiribosomal and Antibacterial Activity
Tetrahedron. 2023 Apr 6;135:133330. doi: 10.1016/j.tet.2023.133330. Epub 2023 Feb 23.ABSTRACTThe design, synthesis and antiribosomal and antibacterial activity of two novel glycosides of the aminoglycoside antibiotic paromomycin are described. The first carries of 4-amino-4-deoxy-β-D-xylopyranosyl moiety at the paromomycin 4'-position and is approximately two-fold more active than the corresponding β-D-xylopyranosyl derivative. The second is a 4'-(β-D-xylopyranosylthio) derivative of 4'-deoxyparomomycin that is unexpectedly less active than the simple β-D-xylopyranosyl derivative, perhaps because of the insertion of th...
Source: Tetrahedron - April 10, 2023 Category: Chemistry Authors: Rukshana Mohamad-Ramshan Chennaiah Ande Takahiko Matsushita Klara Haldimann Andrea Vasella Sven N Hobbie David Crich Source Type: research
The Analysis of Two Distinct Strategies toward the Enantioselective Formal Total Synthesis of (+)-Gelsenicine
Tetrahedron. 2023 Mar 21;134:133278. doi: 10.1016/j.tet.2023.133278. Epub 2023 Jan 21.ABSTRACTA full account of a formal enantioselective total synthesis of (+)-gelsenicine is described. Separate strategies based on catalytic cycloisomerization as the central step are considered. One plan involves chirality transfer from enantioenriched substrates, while the other employs asymmetric catalysis. The chirality transfer strategy is less effective, while in the latter, phosphoramidite- and bisphosphine-gold complexes are tested and ultimately provide a key intermediate in high enantiopurity in our Gelsemium alkaloid syntheses.P...
Source: Tetrahedron - April 10, 2023 Category: Chemistry Authors: Haofan Ji Phil C Knutson Christopher M Harrington Yan-Ting Ke Eric M Ferreira Source Type: research
Synthesis of 4- < em > O < /em > -(4-Amino-4-deoxy- β-D-xylopyranosyl)paromomycin and 4- < em > S < /em > -( β-D-Xylopyranosyl)-4-deoxy-4'-thio-paromomycin and Evaluation of their Antiribosomal and Antibacterial Activity
Tetrahedron. 2023 Apr 6;135:133330. doi: 10.1016/j.tet.2023.133330. Epub 2023 Feb 23.ABSTRACTThe design, synthesis and antiribosomal and antibacterial activity of two novel glycosides of the aminoglycoside antibiotic paromomycin are described. The first carries of 4-amino-4-deoxy-β-D-xylopyranosyl moiety at the paromomycin 4'-position and is approximately two-fold more active than the corresponding β-D-xylopyranosyl derivative. The second is a 4'-(β-D-xylopyranosylthio) derivative of 4'-deoxyparomomycin that is unexpectedly less active than the simple β-D-xylopyranosyl derivative, perhaps because of the insertion of th...
Source: Tetrahedron - April 10, 2023 Category: Chemistry Authors: Rukshana Mohamad-Ramshan Chennaiah Ande Takahiko Matsushita Klara Haldimann Andrea Vasella Sven N Hobbie David Crich Source Type: research
The Analysis of Two Distinct Strategies toward the Enantioselective Formal Total Synthesis of (+)-Gelsenicine
Tetrahedron. 2023 Mar 21;134:133278. doi: 10.1016/j.tet.2023.133278. Epub 2023 Jan 21.ABSTRACTA full account of a formal enantioselective total synthesis of (+)-gelsenicine is described. Separate strategies based on catalytic cycloisomerization as the central step are considered. One plan involves chirality transfer from enantioenriched substrates, while the other employs asymmetric catalysis. The chirality transfer strategy is less effective, while in the latter, phosphoramidite- and bisphosphine-gold complexes are tested and ultimately provide a key intermediate in high enantiopurity in our Gelsemium alkaloid syntheses.P...
Source: Tetrahedron - April 10, 2023 Category: Chemistry Authors: Haofan Ji Phil C Knutson Christopher M Harrington Yan-Ting Ke Eric M Ferreira Source Type: research
Synthesis of 4- < em > O < /em > -(4-Amino-4-deoxy- β-D-xylopyranosyl)paromomycin and 4- < em > S < /em > -( β-D-Xylopyranosyl)-4-deoxy-4'-thio-paromomycin and Evaluation of their Antiribosomal and Antibacterial Activity
Tetrahedron. 2023 Apr 6;135:133330. doi: 10.1016/j.tet.2023.133330. Epub 2023 Feb 23.ABSTRACTThe design, synthesis and antiribosomal and antibacterial activity of two novel glycosides of the aminoglycoside antibiotic paromomycin are described. The first carries of 4-amino-4-deoxy-β-D-xylopyranosyl moiety at the paromomycin 4'-position and is approximately two-fold more active than the corresponding β-D-xylopyranosyl derivative. The second is a 4'-(β-D-xylopyranosylthio) derivative of 4'-deoxyparomomycin that is unexpectedly less active than the simple β-D-xylopyranosyl derivative, perhaps because of the insertion of th...
Source: Tetrahedron - April 10, 2023 Category: Chemistry Authors: Rukshana Mohamad-Ramshan Chennaiah Ande Takahiko Matsushita Klara Haldimann Andrea Vasella Sven N Hobbie David Crich Source Type: research
