Synthesis and enzymatic evaluation of phosphoramidon and its β anomer: Anomerization of α-l-rhamnose triacetate upon phosphitylation

A novel and efficient strategy for the synthesis of phosphoramidon and its β anomer has been developed by manipulating the anomerization of α-l-rhamnose triacetate upon phosphitylation. The experimental results suggest that proton transfer, bond rotation, and N atom are the key factors for the anome...

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Published inBioorganic & medicinal chemistry Vol. 21; no. 21; pp. 6778 - 6787
Main Authors Sun, Qi, Yang, Qingkun, Gong, Shanshan, Fu, Quanlei, Xiao, Qiang
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.11.2013
Elsevier
Subjects
Anomerization
bioactive properties
Biochemistry & Molecular Biology
Chemistry
Chemistry, Medicinal
Chemistry, Organic
Glycopeptide
Glycopeptides - chemical synthesis
Glycopeptides - chemistry
Glycopeptides - metabolism
Hydrogen-Ion Concentration
Kinetics
Life Sciences & Biomedicine
Pharmacology & Pharmacy
Phosphoramidate
Phosphoramidite
Phosphoramidon
Physical Sciences
Protein Binding
Protons
rhamnose
Rhamnose - chemistry
Science & Technology
Stereoisomerism
Temperature
Thermolysin - antagonists & inhibitors
Thermolysin - metabolism
Anomerization
Phosphoramidate
Glycopeptide
Phosphoramidite
Phosphoramidon
COMPLEX
THERMOLYSIN
ANALOGS
ACID-CATALYZED HYDROLYSIS
TRANSITION-STATE
KINETICS
CHEMICAL-SYNTHESIS
INHIBITOR
BINDING
DERIVATIVES
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Abstract A novel and efficient strategy for the synthesis of phosphoramidon and its β anomer has been developed by manipulating the anomerization of α-l-rhamnose triacetate upon phosphitylation. The experimental results suggest that proton transfer, bond rotation, and N atom are the key factors for the anomerization. The determined Ki and Kd values establish that phosphoramidon prepared by this method possesses excellent biological activity, and indicate that the contacts of rhamnose moiety with the enzyme have limited contribution to the binding.
AbstractList A novel and efficient strategy for the synthesis of phosphoramidon and its β anomer has been developed by manipulating the anomerization of α-l-rhamnose triacetate upon phosphitylation. The experimental results suggest that proton transfer, bond rotation, and N atom are the key factors for the anomerization. The determined Ki and Kd values establish that phosphoramidon prepared by this method possesses excellent biological activity, and indicate that the contacts of rhamnose moiety with the enzyme have limited contribution to the binding.
A novel and efficient strategy for the synthesis of phosphoramidon and its beta anomer has been developed by manipulating the anomerization of alpha-L-rhamnose triacetate upon phosphitylation. The experimental results suggest that proton transfer, bond rotation, and N atom are the key factors for the anomerization. The determined K-i and K-d values establish that phosphoramidon prepared by this method possesses excellent biological activity, and indicate that the contacts of rhamnose moiety with the enzyme have limited contribution to the binding. (C) 2013 Elsevier Ltd. All rights reserved.
A novel and efficient strategy for the synthesis of phosphoramidon and its β anomer has been developed by manipulating the anomerization of α-l-rhamnose triacetate upon phosphitylation. The experimental results suggest that proton transfer, bond rotation, and N atom are the key factors for the anomerization. The determined Kᵢ and Kd values establish that phosphoramidon prepared by this method possesses excellent biological activity, and indicate that the contacts of rhamnose moiety with the enzyme have limited contribution to the binding.
Author Fu, Quanlei
Yang, Qingkun
Gong, Shanshan
Sun, Qi
Xiao, Qiang
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Issue 21
Keywords Anomerization
Phosphoramidate
Glycopeptide
Phosphoramidite
Phosphoramidon
COMPLEX
THERMOLYSIN
ANALOGS
ACID-CATALYZED HYDROLYSIS
TRANSITION-STATE
KINETICS
CHEMICAL-SYNTHESIS
INHIBITOR
BINDING
DERIVATIVES
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Snippet A novel and efficient strategy for the synthesis of phosphoramidon and its β anomer has been developed by manipulating the anomerization of α-l-rhamnose...
A novel and efficient strategy for the synthesis of phosphoramidon and its beta anomer has been developed by manipulating the anomerization of alpha-L-rhamnose...
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SubjectTerms Anomerization
bioactive properties
Biochemistry & Molecular Biology
Chemistry
Chemistry, Medicinal
Chemistry, Organic
Glycopeptide
Glycopeptides - chemical synthesis
Glycopeptides - chemistry
Glycopeptides - metabolism
Hydrogen-Ion Concentration
Kinetics
Life Sciences & Biomedicine
Pharmacology & Pharmacy
Phosphoramidate
Phosphoramidite
Phosphoramidon
Physical Sciences
Protein Binding
Protons
rhamnose
Rhamnose - chemistry
Science & Technology
Stereoisomerism
Temperature
Thermolysin - antagonists & inhibitors
Thermolysin - metabolism
Title Synthesis and enzymatic evaluation of phosphoramidon and its β anomer: Anomerization of α-l-rhamnose triacetate upon phosphitylation
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