- β-Lactam derivatives as enzyme inhibitors: N-substituted derivatives of (S)-4-oxoazetidine-2-carboxylate as inhibitors of elastase and papain
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N-Alkyl and N-acyl substituted 4-oxoazetidine-2-carboxylates are synthesized and evaluated as inhibitors of the proteases porcine pancreatic elastase (PPE) and papain. The compounds are obtained by alkylation or acylation at the nitrogen of benzyl (S)-4-oxoazetidine-2-carboxylate, which is synthesized by a modified literature procedure. The enzymatic assays prove some derivatives to be effective inhibitors of PPE and/or papain. The N-BOC protected amino acid derivatives 10 and 13 inhibit PPE reversibly with K(I)-values in the micromolar range. On the other hand, papain is inactivated irreversibly by benzyl (S)-2-(benzyloxycarbonyl)azetidin-1-acetate (6).
- Achilles,Schneider,Schirmeister,Otto
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p. 798 - 802
(2007/10/03)
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- Studies on the Alkylation of Dipeptide Substrates
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Alkylation of anions derived from dipeptides with a glycine at the C-terminus have been investigated.A hydrocarbon sedition in the N-terminal residue does impart some asymmetric induction.The use of a chiral ester derivative provides the potential for double asymmetric induction and good selectivity.With an aspartyl residue at the N-terminus, problems were encountered due to competing side reactions.The use of an azetidione could circumvent some of these, but the observed induction was not high.
- Ager, David J.,Froen, Diane E.,Klix, Russell C.,Zhi, Benxin,McIntosh, John M.,Thangarasa, Rasiah
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p. 1975 - 1982
(2007/10/02)
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- STEREOSPECIFIC SYNTHESIS OF DEALANYLALAHOPCIN
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The first synthesis of the novel α-amino acid dealanylalahopcin starting from (L)-aspartic acid is described.
- Baldwin, Jack E.,Adlington, Robert M.,Gollins, David W.,Schofield, Christopher J.
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p. 4733 - 4748
(2007/10/02)
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- Process for the preparation of 1-carbapenems and intermediates via silyl-substituted dithioacetals
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Disclosed is a process for the total synthesis of 1-carbapenem antibiotics (I) from L-aspartic acid via central intermediates II and III: STR1 wherein R is hydrogen, a pharmaceutically acceptable ester moiety or salt cation, or a readily removable blocking group; R6, R7 and R8 are, inter alia, independently selected from the group consisting of hydrogen, alkyl, alkenyl, aryl and aralkyl; R1' and Re are hydrogen, or a readily removable protecting group; Ra, Rb and Rc are selected from alkyl, aryl or aralkyl.
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- 3-[1-Hydroxyethyl]-4-carboxymethyl-azetidin-2-one
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In a process for the total synthesis of thienamycin from L-aspartic acid via intermediate III: STR1 there is disclosed a process for preparing III via STR2 wherein R is a protecting group.
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- Process for the preparation of 1-carbapenems and intermediates via trithioorthoacetates
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Disclosed is a process for the total synthesis of 1-carbapenem antibiotics (I) from L-aspartic acid via intermediates II and III: STR1 wherein R is hydrogen, a pharmaceutically acceptable ester moiety or salt cation, or a readily removable blocking group; R6 and R7 are, inter alia, independently selected from the group consisting of hydrogen, alkyl, alkenyl, aryl and aralkyl; R1' is hydrogen or a protecting group; and Ra, Rb and Rc are independently selected from alkyl, aryl and aralkyl.
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- Process for preparing 7-(1-hydroxyethyl)-3-(2-aminoethylthio)-1-carbadethiaceph-3-em-3-carboxylic acid and intermediate therefor
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Disclosed is a process for preparing 7-(1-hydroxethyl)-3-(2-aminoethylthio)-1-carbadethiaceph-3-em-3-carboxylic acid and its pharmaceutically acceptable salts and esters (I) by total synthesis starting with L-aspartic acid and proceeding via intermediate II: STR1 R=blocking group
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- Process for the preparation of thienamycin and intermediates
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Disclosed is a process for the total synthesis of thienamycin from L-aspartic acid via intermediate III: STR1 R=H, blocking group or salt cation.
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- 4-Iodomethylazetidin-2-one
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Disclosed is a process for preparing 7-(1-hydroxethyl)-3-(2-aminoethylthio)-1-carbadethiaceph-3-em-3-carboxylic acid and its pharmaceutically acceptable salts and esters (I) by total synthesis starting with L-aspartic acid and proceeding via intermediates II and IIa (4-iodomethylazetidin-2-one): STR1
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