United States of America, As Represented by the Secretary of Agriculture

Neil P Price

Timothy D Leathers

Christopher D Skory

Michael A Jackson

Kenneth M Bischoff

Pennapa Manitchotpisit

John P Bannantine

Cletus P Kurtzman

Tsung Min Kuo

Trina M Hartman

Karen J Ray

The invention relates to new tunicamycin structures comprising N-acyl groups metabolically integrated into the terminus of the TUN via thebranched chain fatty acid pathways and variants thereof, and methods of preparing such new tunicamycin structures. The invention further relates to antibacterial compositions comprising such new tunicamycin structures, and methods for using such antibacterial compositions for killing Gram-positive bacteria.

Omega-alicyclic tunicamycins and analogs

Disclosed are C-glycoside amine derivatives of the formula:R&#x2014;CH&#x2014;C(CH)&#x2014;NH&#x2014;Rwherein R is a saccharide (e.g., as described in U.S. Pat. No. 8,314,219) and Ris an acyl moiety derived from any ketone of the formula R&#x2014;C(O)&#x2014;Rwherein Ris C1 to C22 straight or branched chain hydrocarbon which may be saturated or unsaturated. In addition, a method for making the C-glycoside amine derivatives involving (1) reacting a saccharide (e.g., glucose) C-glycoside ketone with a catalyst (e.g., Rh), about 10 to about 25 fold excess NH, and an organic solvent (e.g., methanol) to form a saccharide C-glycoside amine, and (2) reacting said saccharide C-glycoside amine with a catalyst (e.g., Rh), an organic solvent (e.g., methanol), and an acyl moiety derived from any ketone of the formula R&#x2014;C(O)&#x2014;Rwherein Ris C1 to C22 straight or branched chain hydrocarbon which may be saturated or unsaturated to form said C-glycoside amine derivative.

C-glycoside amine derivatives and methods of making

The present disclosure provides methods for producing bioproducts from novel genetically altered strains of. Methods and materials for the construction of these strains, examination of the bioproducts and analysis and isolation of the bioproducts from genetically altered strains is provided. Genetically alteredstrains in which one or more genes encoding biosynthetic enzymes are knocked out is detailed and the benefits of using such strains described.

Methods and strains for producing bioproducts in

Compounds, called liamocins from, having the general structure in Formula 1 are disclosed. where Ris either COCHor H; and Ris between two to ten O-linked 3,5-dihydroxydecanoate; and Rcan be a polyol (e.g., L- or D-glycerol, L- or D-threitol, L- or D-erythritol, L- or D-arabitol, L- or D-xylitol, L- or D-lyxitol, L- or D-ribitol, L- or D-allitol, L- or D-altritol, L- or D-mannitol, L- or D-iditol, L- or D-gulitol, L- or D-glucitol (also called sorbitol), L- or D-galactitol (also called dulcitol), and L- or D-talitol), 2-amino-D-mannitol, 2N-acetylamino-D-mannitol, L-rhamnitol, or D-fucitol; except when Ris D-mannitol, Ris not 2 nor 3 O-linked 3,5-dihydroxydecanoate chains. These liamocins described above in addition to D-mannitol liamocin A1, D-mannitol liamocin A2, D-mannitol liamocin B1, and D-mannitol liamocin B2, alone or in combination with each other, can be used to kill certain bacteria and to treat certain bacterial infections.

Oils having antibacterial activity

Tunicamycin related compounds having an acyl chain double bond reduced and/or having an acyl chain double bond and an uracil ring double bond reduced are described as well as methods of making these tunicamycin related compounds. These tunicamycin related compounds are not toxic to eukaryotic cells and can be used to kill Gram-positive bacteria, alone or in combination with other antibiotics. Use of these tunicamycin related compounds to kill Gram-positive bacteria, treat Gram-positive bacterial diseases, and disinfect objects or surfaces are described. In addition, naturally-occurring streptovirudin compounds are not toxic to eukaryotic cells and can be used to kill Gram-positive bacteria, alone or in combination with other antibiotics.

Tunicamycin related compounds with anti-bacterial activity

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Novel compounds, called liamocins from, having the general structure in Formula 1 are disclosed. where Ris either COCHor H; and Ris between two to ten O-linked 3,5-dihydroxydecanoate; and Rcan be a polyol (e.g., L- or D-glycerol, L- or D-threitol, L- or D-erythritol, L- or D-arabitol, L- or D-xylitol, L- or D-lyxitol, L- or D-ribitol, L- or D-allitol, L- or D-altritol, L- or D-mannitol, L- or D-iditol, L- or D-gulitol, L- or D-glucitol (also called sorbitol), L- or D-galactitol (also called dulcitol), and L- or D-talitol), 2-amino-D-mannitol, 2N-acetylamino-D-mannitol, L-rhamnitol, or D-fucitol; except when Ris D-mannitol, Ris not 2 nor 3 O-linked 3,5-dihydroxydecanoate chains. These liamocins described above in addition to D-mannitol liamocin A1, D-mannitol liamocin A2, D-mannitol liamocin B1, and D-mannitol liamocin B2, alone or in combination with each other, can be used to kill certain bacteria and to treat certain bacterial infections.

Open chain sophorolipids may be produced by fermentation withsp. NRRL Y-27208 or. Dimers and trimers of sophorolipids are also produced. The sophorolipds are produced by inoculating a fermentation medium comprising a carbon source and a lipid, withorspecies NRRL Y-27208, and incubating under aerobic conditions and for a period of time effective to produce an open chain sophorolipid in the medium. The sophorolipids may be subsequently recovered from the fermentation medium.

Fermentative production of sophorolipids from soybean and other vegetable oils

Alkyl ethers are produced directly from polyols or their salts in a single step reaction, or alternatively, the polyols are first converted to a ketal or acetal derivative which comprises at least one free hydroxyl moiety and one or more ketal or acetal moieties. In either embodiment, the polyol, its salt, or its ketal or acetal derivative is reacted with an alkylating agent to produce a first alkoxy polyol ether comprising one or more alkoxy moieties formed at the sites of the free hydroxyl moieties. Ethers prepared from the polyol ketal or acetal derivatives retain their ketal or acetal moieties, which may be hydrolyzed to additional free hydroxyls and reacted with alkylating agent to produce a second alkoxy polyol ether. Alkyl tosylates are preferred alkylating agents. The spent alkylating agents may also be recovered and regenerated. Recovered alkoxy polyol ethers may be used as renewable fuels, solvents and lubricants.

Carbohydrate and polyol ethers as renewable oils, greases, and liquid fuels

C-glycoside keto-amide derivatives, including C-glycoside keto-hydrazones and C-glycoside keto-oximes, may be prepared from plant or animal lipids and saccharides. These C-glycoside keto-amide derivatives are of the formula: wherein:

Green detergents from agriculture-based lipids and sugars

'Locked-ring' C-glycoside derivatives may be prepared wherein the ring of the sugar molecule remains intact without the need for any protecting groups. These C-glycoside derivatives may be produced by first reacting an aldose reducing sugar, which may be a hexose or a pentose, with a &#x3b2;-diketone to form a C-glycoside ketone. The C-glycoside ketone is then reacted with a ketone reactive compound, such as a hydrazine or hydroxylamine, optionally linked to a detectable label, to form a C-glycoside derivative wherein the ketone reactive compound is conjugated to the C-glycoside at the site of the ketone. The aldose reducing sugar used in the first reaction may a simple pentose or hexose monosaccharide, or it may be optionally substituted.

Growing community of inventors

Edelstein, IL, United States of America

Neil P Price