Synthesis of P(1)-Citronellyl-P(2)-alpha-D-pyranosyl pyrophosphates as potential substrates for the E. coli undecaprenyl-pyrophosphoryl-N-acetylglucoseaminyl transferase MurG.
Publication
, Journal Article
Cudic, P; Behenna, DC; Yu, MK; Kruger, RG; Szewczuk, LM; McCafferty, DG
Published in: Bioorganic & Medicinal Chemistry Letters
December 2001
P(1)-Citronellyl-P(2)-alpha-D-pyranosyl pyrophosphates containing alpha-D-N-acetylglucoseaminyl, alpha-D-glucosyl, and alpha-D-N-acetylmuramyl carbohydrates were synthesized and used in substrate specificity studies of the Escherichia coli MurG enzyme. Oxalyl chloride activation of citronellyl phosphate for coupling to alpha-D-pyranose-1-phosphates resulted in markedly improved yields over traditional Khorana-Moffatt and diphenyl chlorophosphate activation strategies.
Duke Scholars
Published In
Bioorganic & Medicinal Chemistry Letters
DOI
EISSN
1464-3405
ISSN
0960-894X
Publication Date
December 2001
Volume
11
Issue
24
Start / End Page
3107 / 3110
Related Subject Headings
- Substrate Specificity
- Spectrometry, Mass, Electrospray Ionization
- N-Acetylglucosaminyltransferases
- Medicinal & Biomolecular Chemistry
- Magnetic Resonance Spectroscopy
- Escherichia coli
- Diphosphates
- Bacterial Outer Membrane Proteins
- 1115 Pharmacology and Pharmaceutical Sciences
- 0305 Organic Chemistry
Citation
APA
Chicago
ICMJE
MLA
NLM
Cudic, P., Behenna, D. C., Yu, M. K., Kruger, R. G., Szewczuk, L. M., & McCafferty, D. G. (2001). Synthesis of P(1)-Citronellyl-P(2)-alpha-D-pyranosyl pyrophosphates as potential substrates for the E. coli undecaprenyl-pyrophosphoryl-N-acetylglucoseaminyl transferase MurG. Bioorganic & Medicinal Chemistry Letters, 11(24), 3107–3110. https://doi.org/10.1016/s0960-894x(01)00653-9
Cudic, P., D. C. Behenna, M. K. Yu, R. G. Kruger, L. M. Szewczuk, and D. G. McCafferty. “Synthesis of P(1)-Citronellyl-P(2)-alpha-D-pyranosyl pyrophosphates as potential substrates for the E. coli undecaprenyl-pyrophosphoryl-N-acetylglucoseaminyl transferase MurG.” Bioorganic & Medicinal Chemistry Letters 11, no. 24 (December 2001): 3107–10. https://doi.org/10.1016/s0960-894x(01)00653-9.
Cudic P, Behenna DC, Yu MK, Kruger RG, Szewczuk LM, McCafferty DG. Synthesis of P(1)-Citronellyl-P(2)-alpha-D-pyranosyl pyrophosphates as potential substrates for the E. coli undecaprenyl-pyrophosphoryl-N-acetylglucoseaminyl transferase MurG. Bioorganic & Medicinal Chemistry Letters. 2001 Dec;11(24):3107–10.
Cudic, P., et al. “Synthesis of P(1)-Citronellyl-P(2)-alpha-D-pyranosyl pyrophosphates as potential substrates for the E. coli undecaprenyl-pyrophosphoryl-N-acetylglucoseaminyl transferase MurG.” Bioorganic & Medicinal Chemistry Letters, vol. 11, no. 24, Dec. 2001, pp. 3107–10. Epmc, doi:10.1016/s0960-894x(01)00653-9.
Cudic P, Behenna DC, Yu MK, Kruger RG, Szewczuk LM, McCafferty DG. Synthesis of P(1)-Citronellyl-P(2)-alpha-D-pyranosyl pyrophosphates as potential substrates for the E. coli undecaprenyl-pyrophosphoryl-N-acetylglucoseaminyl transferase MurG. Bioorganic & Medicinal Chemistry Letters. 2001 Dec;11(24):3107–3110.
Published In
Bioorganic & Medicinal Chemistry Letters
DOI
EISSN
1464-3405
ISSN
0960-894X
Publication Date
December 2001
Volume
11
Issue
24
Start / End Page
3107 / 3110
Related Subject Headings
- Substrate Specificity
- Spectrometry, Mass, Electrospray Ionization
- N-Acetylglucosaminyltransferases
- Medicinal & Biomolecular Chemistry
- Magnetic Resonance Spectroscopy
- Escherichia coli
- Diphosphates
- Bacterial Outer Membrane Proteins
- 1115 Pharmacology and Pharmaceutical Sciences
- 0305 Organic Chemistry