93527-55-0Relevant academic research and scientific papers
Application of the N-dibenzyl protective group in the preparation of β-lactam pseudopeptides
Frlan, Rok,Hrast, Martina,Gobec, Stanislav
, (2019/04/05)
Despite the great importance of β-lactam antibiotics, there is still a limited number of synthetic approaches for the formation of β-lactam–containing dipeptides. In this study, we report upon the stereoselective preparation of β-lactam–containing pseudopeptides, where different reaction conditions and NH2 protective groups were tested to obtain compounds that contain 3-amino-azetidin-2-one. We demonstrate that the protective group is essential for the outcome of the reaction. Successful implementation of dibenzyl-protected serine-containing dipeptides through the Mitsunobu reaction can provide the desired products at high yields and stereoselectivity.
LEFT-HANDED GAMMA-PEPTIDE NUCLEIC ACIDS, METHODS OF SYNTHESIS AND USES THEREFOR
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Paragraph 0020; 00110, (2015/11/27)
A method of making optically pure preparations of chiral γΡΝΑ (gamma peptide nucleic acid) monomers is provided. Nanostructures comprising chiral γΡΝΑ structures also are provided. Methods of amplifying and detecting specific nucleic acids, including in situ methods are provided as well as compositions and kits useful in those methods. Lastly, methods of converting nucleobase sequences from right-handed helical PNA, nucleic acid and nucleic acid analog structures to left-handed γΡΝΑ, and vice- versa, are provided.
Improved enantioselective synthesis of protected (3S,4S)-4-amino-3,5- dihydroxypentanoic acid (ADPA)
Mei, Duo,Zhang, Wei,Li, Yingxia
experimental part, p. 1099 - 1105 (2010/04/29)
An improved enantioselective synthesis of protected (3S,4S)-4-amino-3,5- dihydroxypentanoic acid (ADPA) from L-serine has been developed. Enantioselectivity is improved by replacing the methyl ester with the tert-butyl ester and using neutral magnesium salt of esters to give β-keto ester.
Discovery and preclinical evaluation of [4-[[1-(3-fluorophenyl)methyl]-1H- indazol-5-ylamino]-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl]carbamic acid, (3S)-3-morpholinylmethyl ester (BMS-599626), a selective and orally efficacious inhibitor of human epide
Gavai, Ashvinikumar V.,Fink, Brian E.,Fairfax, David J.,Martin, Gregory S.,Rossiter, Lana M.,Holst, Christian L.,Kim, Soong-Hoon,Leavitt, Kenneth J.,Mastalerz, Harold,Han, Wen-Ching,Norris, Derek,Goyal, Bindu,Swaminathan, Shankar,Patel, Bharat,Mathur, Arvind,Vyas, Dolatrai M.,Tokarski, John S.,Chiang, Yu,Oppenheimer, Simone,Hongjian, Zhang,Marathe, Punit,Fargnoli, Joseph,Lee, Francis Y.,Wong, Tai W.,Vite, Gregory D.
supporting information; experimental part, p. 6527 - 6530 (2010/03/26)
Structure-activity relationships in a series of 4-[1H-indazol-5-ylamino] pyrrolo[2,1-f][1,2,4]triazine-6-carbamates identified dual human epidermal growth factor receptor (HER)1/HER2 kinase inhibitors with excellent biochemical potency and kinase selectiv
Synthesis of Enterochelin
Rogers, Henry J.
, p. 3073 - 3076 (2007/10/03)
Enterochelin (enterobactin), the cyclic trilactone of N-(2,3-dihydroxybenzoyl)-L-serine 6, an important enterobacterial iron-transporting compound, has been synthesised from N,N-dibenzyl-L-serine 2 in four steps.The protected amino acid was oligomerised using N,N-dicyclohexylcarbodiimide in a high-dilution procedure yielding a mixture of di-, tri- and tetra-lactones.The trilactone 3b was deprotected by hydrogenolysis and the resultant amine 4 was acylated with 2,3-dibenzyloxybenzoyl chloride to yield hexa-O-benzylenterochelin 5.This upon hydrogenolysis gave enterochelin in moderate yield.
Stereochemistry of Catabolism of the DNA Base Thymine and of the Anticancer Drug 5-Fluorouracil
Gani, David,Hitchcock, Peter B.,Young, Douglas W.
, p. 1363 - 1372 (2007/10/02)
(2S)-3-Amino-2-methylpropanoic acid (6) and (2RS,3S)--3-amino-2-methylpropanoic acid (14) have been synthesized and used to provide an assay which shows that the catabolism of the DNA base thymine (1; R = Me) proceeds by overall anti addition of hydrogen to the pyrimidine at the si face at C-5 and the si face at C-6.X-Ray structure analysis of a derivative of the product of reaction of N,N-dibenzyl-L-serine methyl ester (15; R = Me) with (diethylamino)sulphur trifluoride followed by deprotection has shown it to be (2R)-3-amino-2-fluoropropanoic acid (19; R = H).This was identical with the product of catabolism of the anti-cancer drug 5-fluorouracil (1; R = F).Esters of (2R,3S)-- and (2R,3R)--3-amino-2-fluoropropanoic acids have been synthesized and used to provide an assay which shows that catabolism of the anti-cancer drug 5-fluorouracil (1; R = F) proceeds with the same absolute stereochemistry as is found in catabolism of thymine (1; R = Me).
