New synthesis of L-2-amino-3-oxalylaminopropionic acid, the Lathyrus sativus neurotoxin

Haskell, Betty E.; Bowlus, Stephen B.

doi:10.1021/jo00863a042

Cited by 30 publications

(6 citation statements)

References 3 publications

(5 reference statements)

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“…Treatment of 3a with metallic sodium in liquid ammonia induced complete degradation of the starting material. Similarly, heating of 3a at 70 °C in an acetic acid solution containing HBr for 8 h resulted in complete decomposition of 3a 37. When 3a was treated with LiAlH 4 in THF (reflux, 8 h),38 N–S bond cleavage occurred, but the alkoxysilane functionality was also totally unmasked, which led to β‐amino alcohol 4 in 70 % yield (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Mild Electrochemical Deprotection of N‐Phenylsulfonyl N‐Substituted Amines Derived from (R)‐Phenylglycinol

et al. 2007

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The electrochemical reduction of N‐phenylsulfonyl N‐substituted amines in a protic medium under constant cathodic potential was found to be a mild desulfonylation method, which is able to challenge the chemical ones. The influence of the nature of the N‐substituents was considered in order to clarify the mechanistic aspects and to evaluate the scope of the method.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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Section: Resultsmentioning

confidence: 99%

Mild Electrochemical Deprotection of N‐Phenylsulfonyl N‐Substituted Amines Derived from (R)‐Phenylglycinol

et al. 2007

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“…Having defined the stereochemistry of allylated aspartate 10 unambiguously, we converted it into diacid 18 by sequential reaction with TFA and then LiOH in aqueous methanol. Unfortunately, all efforts to remove the N-protecting group, such as reaction with 48% HBr in acetic acid, failed to give products that were easily separable, presumably due to side-reactions involving the double bond. Removal of the N -carbobenzoxy protecting group, however, under standard catalytic hydrogen transfer conditions, proceeded with concomitant reduction of the double bond to give 3- n -propyl aspartate 19 (Scheme ) …”

Section: Chemistrymentioning

confidence: 99%

Mapping the Aspartic Acid Binding Site of Escherichia coli Asparagine Synthetase B Using Substrate Analogs

et al. 1996

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Novel inhibitors of asparagine synthetase, that will lower circulating levels of blood asparagine, have considerable potential in developing new protocols for the treatment of acute lymphoblastic leukemia. We now report the indirect characterization of the aspartate binding site of Escherichia coli asparagine synthetase B (AS-B) using a number of stereochemically, and conformationally, defined aspartic acid analogs. Two compounds, prepared using novel reaction conditions for the stereospecific beta-functionalization of aspartic acid diesters, have been found to be competitive inhibitors with respect to aspartate in kinetic studies on AS-B. Chemical modification experiments employing [(fluorosulfonyl)benzoyl]adenosine (FSBA), an ATP analog, demonstrate that both inhibitors bind to the aspartate binding site of AS-B. Our results reveal that large steric alterations in the substrate are not tolerated by the enzyme, consistent with the failure of previous efforts to develop AS inhibitors using random screening approaches, and that all of the ionizable groups are placed in close proximity in the bound conformation of aspartate.

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“…We then considered the methods used for deprotection of the N ‐SO 2 Ph group (see the Supporting Information for details). Regarding the acetic acid solution containing HBr, the N–S bond cleavage occurred and 10b was isolated with a yield of 70 %. Adding phenol (5.0 equiv.)…”

Section: Resultsmentioning

confidence: 99%

Deoxyalkoxyamination of Alcohols for the Synthesis of N‐Alkoxy‐N‐alkylbenzenesulfonamides

Sun

et al. 2018

Eur J Org Chem

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A novel protocol for the deoxyalkoxyamination of alcohols has been developed, using N‐alkoxybenzenesulfonimide (NOSI) as both a sulfonyl transfer reagent and an alkoxyamine source, accessing a diverse range of N‐alkoxy‐N‐alkylbenzenesulfonamides with excellent isolated yields. This method is characterized by metal‐free reaction, scalability, and waste‐balance. Chiral substrates are converted with excellent levels of stereochemical inversion. NOSI could be generated in situ during the reaction as a stable reagent if a three‐component one‐pot reaction was designed. Exploiting this approach to run intramolecular reactions offered various N‐protected isoxazolidines. In addition, valuable O‐alkyl hydroxylamines (or isoxazolidines) were obtained through a neutral strategy of desulfonylation of the products.

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New synthesis of L-2-amino-3-oxalylaminopropionic acid, the Lathyrus sativus neurotoxin

Cited by 30 publications

References 3 publications

Mild Electrochemical Deprotection of N‐Phenylsulfonyl N‐Substituted Amines Derived from (R)‐Phenylglycinol

Mild Electrochemical Deprotection of N‐Phenylsulfonyl N‐Substituted Amines Derived from (R)‐Phenylglycinol

Mapping the Aspartic Acid Binding Site of Escherichia coli Asparagine Synthetase B Using Substrate Analogs

Deoxyalkoxyamination of Alcohols for the Synthesis of N‐Alkoxy‐N‐alkylbenzenesulfonamides

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