University of California

Los Alamos National Security, LLC

New Mexico Highlands University

Other

Cambridge Isotope Laboratories, Inc.

Rodolfo Antonio Martinez

Clifford J Unkefer

Marc A Alvarez

Pat J Unkefer

Louis A Silks

Thomas J Knight

David R Glass

Merritt C Helvenston

John R Juarez

Jurgen G Schmidt

Jose C De Baca

Kenneth Edmund Tortolani

Robert Atcher

Nathan Philip Martinez

David Rembert Glass

Jose C′ De Baca

Mark Minton

Frank Elbert Anderson, Iii

Erick Gabriel Ortiz

A synthesis method comprises opening an anhydride to a 4-carbon acid-amide, removing ethanol soluble products, treating the resulting 4-amino-2-methylene-4-oxo-butanoic acid with Ozone in water, and evaporating the ozonolysis products to synthesize 4-amino-2,4-dioxobutanoic acid.

Synthesis of 4-amino-2, 4-dioxobutanoic acid

A process for synthesizing 4-amino-2,4-dioxobutanoic acid involves reacting diethyl oxalate with an alkoxide in ethanol to form a reaction mixture, and afterward adding ethyl cyanoacetate to the reaction mixture and allowing a reaction to proceed under conditions suitable to form a first reaction product of the formula diethyl 2-cyano-3-hydroxy-butenedioate, and then isolating the diethyl 2-cyano-3-hydroxy-butenedioate, and afterward reacting the diethyl-2-cyano-3-hydroxy-butenedioate with an aqueous hydroxide under conditions suitable to form 4-amino-2,4-dioxobutanoic acid.

Preparation of 4-amino-2,4-dioxobutanoic acid

A process for synthesizing 4-amino-2,4-dioxobutanoate involves reacting a dialkyl oxalate with an alkoxide in ethanol to form a reaction mixture, and afterward adding an alkyl cyano acetate to the reaction mixture and allowing a reaction to proceed under conditions suitable to form a first reaction product of the formula diethyl 2-cyano-3-hydroxy-butenedioate, and then isolating the diethyl 2-cyano-3-hydroxy-butenedioate, and afterward reacting the diethyl-2-cyano-3-hydroxy-butenedioate with an aqueous hydroxide under conditions suitable to form 4-amino-2,4-dioxobutanoate. The 4-amino-2,4-dioxobutanoate may be acidified into 4-amino-2,4-dioxobutanoic acid.

A process for synthesizing 4-amino-2,4-dioxobutanoic acid involves reacting diethyl oxalate with sodium ethoxide in ethanol to form a reaction mixture, and afterward adding ethyl cyanoacetate to the reaction mixture and allowing a reaction to proceed under conditions suitable to form a first reaction product of the formula diethyl-2-cyano-3-hydroxy-butenedioate, and then isolating the diethyl-2-cyano-3-hydroxybutenedioate, and afterward reacting the diethyl-2-cyano-3-hydroxy-butenedioate with aqueous sodium hydroxide under conditions suitable to form 4-amino-2,4-dioxobutanoic acid.

The present invention describes a composition including a mixture of L- and D-pyroglutamate stereoisomers in a ratio of L to D of from about 80:20 to about 97:3 , and, a carrier medium for application of the L- and D-pyroglutamate stereoisomers to a target plant. The composition can also be used as a germination medium and may be incorporated into a seed coat for assisting in germination. The present invention further describes a method of increasing the agronomic performance of a target plant by treating a target plant with a composition including a mixture of L- and D-pyroglutamate stereoisomers in a ratio of L to D of from about 80:20 to about 97:3 and a carrier medium for said L- and D-pyroglutamate stereoisomers.

Use of prolines for improving growth and/or yield

The present invention describes a composition including a mixture of L- and D-pyroglutamate stereoisomers in a ratio of L to D of from about 80:20 to about 97:3, and, a carrier medium for application of the L- and D-pyroglutamate stereoisomers to a target plant. The composition can also be used as a germination medium and may be incorporated into a seed coat for assisting in germination. The present invention further describes a method of increasing the agronomic performance of a target plant by treating a target plant with a composition including a mixture of L- and D-pyroglutamate stereoisomers in a ratio of L to D of from about 80:20 to about 97:3 and a carrier medium for said L- and D-pyroglutamate stereoisomers.

A filtration system and method for the remediation of hydrazine from contaminated gas is disclosed. The system is provided in the form of a container with an net port and an outlet port containing absorbent pads or filters or wipes saturated with a solution of a dicarbonyl compound. As contaminated gas passes through the container, hydrazine present within the gas reacts with the dicarbonyl compound and becomes neutralized, thereby resulting in the exit of pure gas that no longer contains hydrazine from the container. The system can remediate hydrazine from ammonia borane to efficiently regenerate spent said ammonia borane from polyborazylene as a hydrogen storage material. The absorbent pads can also be used independently to remove hydrazine liquid spill.

Hydrazine filtration method and system

The chemistry of [C]methyl phenyl sulfide is exploited to produce new isotopically labeled precursors that allow for the facile assembly of a wide range of labeled molecules from simple and relatively inexpensive starting materials. These compounds are applicable to a variety of research areas such as quantum computing, metabolism and materials science.

Single carbon precursor synthons

The present invention is directed to the labeled compounds, wherein C* is each eitherC andC where at least one C* isC, each hydrogen of the methylene group is hydrogen or deuterium, the methyl group includes either zero or three deuterium atoms, Q is sulfide, sulfinyl, or sulfone, Z is an aryl group such as 1-naphthyl, substituted 1-naphthyl, 2-naphthyl, substituted 2-naphthyl, or a phenyl group wherein R, R, R, Rand Rare each independently either hydrogen, a C-Clower alkyl, a halogen, and an amino group such as NH, NHR and NRR' where R and R&#x2032; are each independently either a C-Clower alkyl, a phenyl, and an alkoxy group, and the methyl group can include either zero or three deuterium atoms. The present invention is also directed to the labeled compounds 

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High purity isotopically labeled phosphonic acid esters can be obtained from isotopically enriched Chloro[C]methyl phenyl sulfide The labeled phosphonic acid esters can then be used as precursors for the one step production of labeled vinyl sulfides, labeled vinyl sulfoxides, and labeled vinyl sulfones. The labeled phosphonic acid esters can also be reacted with a variety of aldehydes to produce extended vinyl systems that are isotopically labeled.

Synthesis of phosphonic acid labeled compounds

An air filtration system and method for the remediation of hydrazine from contaminated air. The system is provided in the form of a container with an inlet port and an outlet port containing absorbent pads or filters or wipes saturated with a solution of a dicarbonyl compound. As contaminated air passes through the container, hydrazine present within the air reacts with the dicarbonyl compound and becomes neutralized, thereby resulting in the exit of pure air from the container. The absorbent pads can also be used independently to remove hydrazine liquid spill.

Air filtration and absorption method and system for the remediation of hydrazine

The use of vinyl sulfides, sulfoxides and sulfones in synthetic chemistry for the production of a wide variety of materials is well known. For example, phenyl vinyl sulfides, sulfoxides and sulfones have been used for the synthesis of important heterocycles, in combinatorial chemistry and as Diels-Alder adducts. Although these compounds have been used extensively for a variety of applications, the isotopically labeled versions have not been reported. A simple route for the isotopically labeled production of these important building blocks has been developed.

Isotopically tagged synons from 2 carbon precursors

Alkoxy[C]methyl phenyl sulfone is a precursor to the production of Lithium (E)-&#x3b2;-Alkoxy[1,2,3-C]acrylate and thence Alkoxy (E)-&#x3b2;-Alkoxy[1,2,3-C]acrylate. Alkoxy (E)-&#x3b2;-Alkoxy[1,2,3-C]acrylate can then serve as a precursor for the production of a number of other isotopically labeled compounds. Similar chemistry using Alkoxy[C]methyl phenyl sulfone as the precursor can yieldC labeled compounds. High purity precursors ensure that the new compounds are also highly pure.

Three carbon precursor synthons

Isotopically labeled alpha-keto acids and esters are disclosed herein. Also disclosed are methods of synthesizing isotopically labeled alpha-keto acids and esters.

Synthesis of isotopically labeled alpha-keto acids and esters

The present invention is directed to labeled compounds of the formulae  wherein R, R, R, Rand Rare each independently selected from the group consisting of hydrogen, a C-Clower alkyl, a halogen, and an amino group selected from the group consisting of NH, NHR and NRR' where R and R&#x2032; are each independently selected from the group consisting of a C-Clower alkyl, an aryl, and an alkoxy group, and X is selected from the group consisting of hydrogen, a C-Clower alkyl group, and a fully-deuterated C-Clower alkyl group.

Growing community of inventors

Santa Fe, NM, United States of America

Rodolfo Antonio Martinez