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N-[双(甲硫基)亚甲基]对甲苯磺酰胺 反应生成N-叔丁氧羰基-N'-甲苯磺酰基-L-精氨酸
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专利信息

专利号:US-7589170-B1
优先权日:1998-09-25
标题 :Synthesis of cyclic peptides
发明人：SMYTHE MARK LESLIE; MEUTERMANS WIM DENIS FRANS; BOURNE GREGORY THOMAS; MCGEARY ROSS PETER
权利人:UNIV QUEENSLAND
摘要:This invention relates to methods for preparing cyclic peptides and peptidomimetic compounds in solution and bound to solid supports, and to cyclic peptide or peptidomimetic libraries for use in drug screening programs. In particular, the invention relates to a generic strategy for synthesis of cyclic peptides or peptidomimetics that enables the efficient synthesis under mild conditions of a wide variety of desired compounds. Two approaches were evaluated for their improvements in solution and solid phase synthesis of small cyclic peptides: positioning reversible N-amide substituents in the sequence; and applying native ligation chemistry in an intramolecular sense. Systematic investigation of the effects of preorganising peptides prior to cyclisation by using peptide cyclisation auxiliaries, and developing new linkers and peptide cyclisation auxiliaries to aid cyclic peptide synthesis gives surprising improvements in both yields and purity of products compared to the prior art methods. The combination of these technologies provides a powerful generic approach for the solution and solid phase synthesis of small cyclic peptides. The ring contraction and N-amide substitution technology of the invention provide improved methods for the synthesis of cyclic peptides and peptidomimetics. When used in conjunction with linker strategies, this combination provides solid-phase avenues to cyclic peptides and peptidomimetics.

专利号:US-4101721-A
优先权日:1976-12-09
标题 :Solid phase synthesis of protected peptides
发明人：RICH DANIEL H; GURWARA SWEET K
权利人:WISCONSIN ALUMNI RES FOUND
摘要:The invention is addressed to the preparation of 3-nitro-4-bromomethyl benzoic acid, as a new compound from which 3-nitro-4-bromomethyl benzoyl amide polystyrene resin can be prepared for solid synthesis of protected peptide acids and amides and separation thereof without cleavage of acid labile protecting groups or decomposition of aromatic acid groups and from which purified polypeptides can be formed.

专利号:US-4062746-A
优先权日:1975-05-07
标 题 :Solid phase synthesis of protected peptides
发明人：RICH DANIEL H; GURWARA SWEET K
权利人:WISCONSIN ALUMNI RES FOUND
摘要:The invention is addressed to the preparation of 3-nitro-4-bromomethyl benzoic acid, as a new compound from which 3-nitro-4-bromomethyl benzoyl amide polystyrene resin can be prepared for solid synthesis of protected peptide acids and amides and separation thereof without cleavage of acid labile protecting groups or decomposition of aromatic acid groups and from which purified polypeptides can be formed.

专利号:US-5886104-A
优先权日:1993-06-18
标题 :Grafted cross-linked polyolefin substrates for peptide synthesis and assays
发明人：PEDERSEN WALTHER BATSBERG; ALMDAL KRISTOFFER; WINTHER LARS; BERG ROLF HENRIK
权利人:FORSKNIINGSCENTER RISO
摘要:A solid support for the solid-phase synthesis of peptides or proteins in high yield and in high purity, suited both to the synthesis of a single peptide or protein and to the parallel and substantially simultaneous synthesis of a plurality thereof, is based on a cross-linked polyolefin, especially polyethylene, substrate, the cross-linking having been obtained by irradiation with high energy electrons or γ radiation or treatment with organic peroxide such as benzoyl peroxide, to which substrate are grafted polymer chains such as polystyrene chains which are functionalized with a chemical functionality facilitating the formation of an anchoring linkage between the polymer moiety and another chemical species. The solid support is also suited for use in solid-phase biosystems, notably bioassays, such as immunoassays, DNA hybridization assays or PCR amplification. The grafted chains may bear substituents which are such that the polymer-grafted cross-linked polyolefin substrate is swellable by water or aqueous media, in other words, hydrophilic, which makes the solid support particularly well suited for assays of the ELISA type.

专利号:US-4786684-A
优先权日:1986-08-21
标题 :Benzylthioether-linked solid support-bound thiol compounds and method for peptide synthesis
发明人：GLASS JOHN D
权利人:SINAI SCHOOL MEDICINE
摘要:A method for the synthesis of sulfydryl-containing peptides which comprises forming a benzylthioether-linked solid support-bound thiol compound having at least one functional group for generating at least one peptide bond, sequentially coupling at least one protected amino acid or peptide to the compound until a peptide having desired amino acid sequence is obtained, and cleaving the benzylthioether linkage to release the peptide from the support with concomitant regenertion of the sulfydryl group in the peptides. The invention also encompasses compounds having the general formula wherein X is H, NH2, or acyl-NHY, said acyl being an amino acid or a peptide; Y is H, COOH, CONHNH2, the ester COOR1 in which R1 is selected from the group consisting of methyl, ethyl, phenyl, ortho-nitrophenyl and para-nitrophenyl, the amide CONH2, or the amide CONHR2 in which R2 is an amino acid or peptide; and providing that X and Y cannot both be H.

专利号:US-4701499-A
优先权日:1983-10-24
标题:Synthesis of N-substituted peptide amides
发明人：KORNREICH WAYNE D; ANDERSON HARRY A; PORTER JOHN S; RIVIER JEAN E F
权利人:SALK INST FOR BIOLOGICAL STUDI
摘要:Peptide N-alkylamides, and other C-terminal N-substituted amides, can be synthesized using solid-phase synthesis on a benzene-containing resin which is suitably methylated. Reactive amino groups are attached directly or indirectly to the methyl groups, for example, such as by reacting commercially available chloromethylated polystyrene resins with an alkylamine to create a resin-amine. The C-terminal amino acid of the desired peptide is linked to the resin-amine via an amide linkage, and the peptide is thereafter built in normal fashion. Treatment of the completed peptide intermediate with HF is effective to both effect deprotection and cleave the peptide from the resin in the form of the N-substituted amide. Examples include peptide N-ethylamides, N-fluoroethylamide, N-anilides and other substituted N-benzylamides.