72776-06-8Relevant academic research and scientific papers
β-Lactam derivatives as enzyme inhibitors: N-substituted derivatives of (S)-4-oxoazetidine-2-carboxylate as inhibitors of elastase and papain
Achilles,Schneider,Schirmeister,Otto
, p. 798 - 802 (2007/10/03)
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).
Studies on the Alkylation of Dipeptide Substrates
Ager, David J.,Froen, Diane E.,Klix, Russell C.,Zhi, Benxin,McIntosh, John M.,Thangarasa, Rasiah
, p. 1975 - 1982 (2007/10/02)
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.
STEREOSPECIFIC SYNTHESIS OF DEALANYLALAHOPCIN
Baldwin, Jack E.,Adlington, Robert M.,Gollins, David W.,Schofield, Christopher J.
, p. 4733 - 4748 (2007/10/02)
The first synthesis of the novel α-amino acid dealanylalahopcin starting from (L)-aspartic acid is described.
Process for the preparation of 1-carbapenems and intermediates via silyl-substituted dithioacetals
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, (2008/06/13)
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.
3-[1-Hydroxyethyl]-4-carboxymethyl-azetidin-2-one
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, (2008/06/13)
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.
Process for the preparation of 1-carbapenems and intermediates via trithioorthoacetates
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, (2008/06/13)
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.
Process for preparing 7-(1-hydroxyethyl)-3-(2-aminoethylthio)-1-carbadethiaceph-3-em-3-carboxylic acid and intermediate therefor
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, (2008/06/13)
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
Process for the preparation of thienamycin and intermediates
-
, (2008/06/13)
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.
4-Iodomethylazetidin-2-one
-
, (2008/06/13)
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
