An efficient and facile synthesis of D-cycloserine substantially free from potential impurities

Awasthi, Arun Kumar; Kumar, Brijesh; Aga, Mushtaq A.; Tripathi, Punit; Reddy, C. Suresh; Kumar, Pramod

doi:10.1007/s10593-018-2197-y

Cited by 4 publications

(4 citation statements)

References 17 publications

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“…Several more modern approaches for the synthesis of enantiomerically pure cycloserines were reported in the 2010s [41–47] . Li et al .…”

Section: Antibacterial Amino Acid‐based Agentsmentioning

confidence: 99%

“…Awasthi et al . reported synthesis of this compound with remarkable purity, under mild reaction conditions [47] . In that approach they used N ‐benzyloxycarbonyl‐protected d ‐serine and transformed it into N ‐protected derivative 11 via cyclization reaction of ω‐hydroxyhydroxamic acid 10 under basic conditions (Scheme 2, path D).…”

Section: Antibacterial Amino Acid‐based Agentsmentioning

confidence: 99%

“…Several more modern approaches for the synthesis of enantiomerically pure cycloserines were reported in the 2010s. [ 41 , 42 , 43 , 44 , 45 , 46 , 47 ] Li et al . proposed an original and efficient synthesis of d ‐cycloserine (Scheme 2 , path A).…”

Section: Antibacterial Amino Acid‐based Agentsmentioning

confidence: 99%

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Amino Acid Based Antimicrobial Agents – Synthesis and Properties

2021

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Structures of several dozen of known antibacterial, antifungal or antiprotozoal agents are based on the amino acid scaffold. In most of them, the amino acid skeleton is of a crucial importance for their antimicrobial activity, since very often they are structural analogs of amino acid intermediates of different microbial biosynthetic pathways. Particularly, some aminophosphonate or aminoboronate analogs of protein amino acids are effective enzyme inhibitors, as structural mimics of tetrahedral transition state intermediates. Synthesis of amino acid antimicrobials is a particular challenge, especially in terms of the need for enantioselective methods, including the asymmetric synthesis. All these issues are addressed in this review, summing up the current state‐of‐the‐art and presenting perspectives fur further progress.

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“…Several more modern approaches for the synthesis of enantiomerically pure cycloserines were reported in the 2010s [41–47] . Li et al .…”

Section: Antibacterial Amino Acid‐based Agentsmentioning

confidence: 99%

Section: Antibacterial Amino Acid‐based Agentsmentioning

confidence: 99%

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Amino Acid Based Antimicrobial Agents – Synthesis and Properties

2021

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“…Continuing our interest in the process research and development of API [[25], [26], [27], [28]] and their impurity profiling [[29], [30], [31]] as a means of pharmaceutical analysis to manufacture high quality drug, herein, we report our investigation towards the formation and control of potential dimer impurity E ( 1 ) in the synthesis of PAN, and a most optimal preparation procedure of dimer impurity. The data obtained will facilitate the optimization of manufacturing processes and the quality control of PAN.…”

Section: Introductionmentioning

confidence: 99%

Prospects to the formation and control of potential dimer impurity E of pantoprazole sodium sesquihydrate

Awasthi

Kumar

Tripathi

et al. 2019

Journal of Pharmaceutical Analysis

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Pantoprazole sodium, a substituted benzimidazole derivative, is an irreversible proton pump inhibitor which is primarily used for the treatment of duodenal ulcers, gastric ulcers, and gastroesophageal reflux disease (GERD). The monographs of European Pharmacopoeia (Ph. Eur.) and United States Pharmacopoeia (USP) specify six impurities, viz. ; impurities A, B, C, D, E and F, respectively for its active pharmaceutical ingredient (API). The identification and synthesis of all impurities except impurity E are well described in the literature; however, there is no report related to impurity E. The prospects to the formation and controlling of impurity E up to ≤0.03% in the synthesis of pantoprazole sodium sesquihydrate (PAN) were discussed in detail for the first time. The present work described the journey towards the successful development of an optimal preparation procedure of dimer impurity E. The most plausible mechanism involved in the formation of impurity E has been proposed.

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