- A practical solid phase synthesis of oligopeptidosulfonamide foldamers
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Oligopeptidosulfonamide foldamers were efficiently synthesized on the solid phase using Fmoc protected β-aminoethanesulfonylchlorides in the presence of N-methylmorpholine. (C) 2000 Elsevier Science Ltd.
- Monnee,Marijne,Brouwer,Liskamp
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Read Online
- Fast and Facile Synthesis of 4-Nitrophenyl 2-Azidoethylcarbamate Derivatives from N-Fmoc-Protected α-Amino Acids as Activated Building Blocks for Urea Moiety-Containing Compound Library
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A fast and facile synthesis of a series of 4-nitrophenyl 2-azidoethylcarbamate derivatives as activated urea building blocks was developed. The N-Fmoc-protected 2-aminoethyl mesylates derived from various commercially available N-Fmoc-protected α-amino ac
- Chen, Ying-Ying,Chang, Li-Te,Chen, Hung-Wei,Yang, Chia-Ying,Hsin, Ling-Wei
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p. 131 - 136
(2017/04/24)
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- A greener, efficient and catalyst-free ultrasonic-assisted protocol for the n-fmoc protection of amines
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A simple, eco-sustainable method for the N-(9-fluorenylmethoxycarbonyl) (N-Fmoc) protection of various structurally amines under ultrasonic irradiation is reported. The corresponding N-Fmoc derivatives were obtained in good to excellent yields within short reaction time. The reaction proceeds without the formation of any side product. Mildness, efficiency and easier work are the main advantages of this new protocol.
- Mansouri, Rachida,Aouf, Zineb,Lakrout, Salah,Berredjem, Malika,Aouf, Nour-Eddine
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p. 546 - 550
(2016/03/19)
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- Probing the Physicochemical Boundaries of Cell Permeability and Oral Bioavailability in Lipophilic Macrocycles Inspired by Natural Products
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Cyclic peptide natural products contain a variety of conserved, nonproteinogenic structural elements such as d-amino acids and amide N-methylation. In addition, many cyclic peptides incorporate γ-amino acids and other elements derived from polyketide synt
- Bockus, Andrew T.,Lexa, Katrina W.,Pye, Cameron R.,Kalgutkar, Amit S.,Gardner, Jarret W.,Hund, Kathryn C.R.,Hewitt, William M.,Schwochert, Joshua A.,Glassey, Emerson,Price, David A.,Mathiowetz, Alan M.,Liras, Spiros,Jacobson, Matthew P.,Lokey, R. Scott
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supporting information
p. 4581 - 4589
(2015/06/25)
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- Alzheimer's disease: Identification and development of β-secretase (BACE-1) binding fragments and inhibitors by dynamic ligation screening (DLS)
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The application of dynamic ligation screening (DLS), a methodology for fragment-based drug discovery (FBDD), to the aspartic protease β-secretase (BACE-1) is reported. For this purpose, three new fluorescence resonance energy transfer (FRET) substrates we
- Fernandez-Bachiller, Maria Isabel,Horatscheck, Andre,Lisurek, Michael,Rademann, Joerg
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p. 1041 - 1056
(2013/07/26)
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- An expedient route for the reduction of carboxylic acids to alcohols employing 1-propanephosphonic acid cyclic anhydride as acid activator
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A simple and efficient method for the synthesis of alcohols from the corresponding carboxylic acids is described. Activation of carboxylic acid with 1-propane phosphonic acid cyclic anhydride (T3P) and subsequent reduction of the intermediate phosphonic anhydride with NaBH4 yield the alcohol in excellent yields with good purity in less duration. Reduction of several alkyl/aryl carboxylic acids and Nα-protected amino acids/peptide acids as well as Nβ-protected amino acids was successfully carried out to obtain corresponding alcohols in good yields and the products characterized. The procedure is mild, safe, simple and the isolation of the products is easy.
- Nagendra,Madhu,Vishwanatha,Sureshbabu, Vommina V.
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experimental part
p. 5059 - 5063
(2012/09/22)
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- A facile synthesis and crystallographic analysis of N-protected β-amino alcohols and short peptaibols
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A facile, efficient and racemization-free method for the synthesis of N-protected β-amino alcohols and peptaibols using N-hydroxysuccinimide active esters is described. Using this method, dipeptide, tripeptide and pentapeptide alcohols were isolated in high yields. The conformations in crystals of β-amino alcohol, dipeptide and tripeptide alcohols were analysed, with a well-defined type III β-turn being observed in the tripeptide alcohol crystals. This method is found to be compatible with Fmoc-, Boc- and other side-chain protecting groups.
- Jadhav, Sandip V.,Bandyopadhyay, Anupam,Benke, Sushil N.,Mali, Sachitanand M.,Gopi, Hosahudya N.
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supporting information; experimental part
p. 4182 - 4187
(2011/06/28)
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- A simple synthesis of N β-Fmoc/Z-amino alkyl thiols and their use in the synthesis of N β-Fmoc/Z-amino alkyl sulfonic acids
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A simple and efficient protocol for the synthesis of Nβ- Fmoc/Z-amino alkyl thiols is described. The approach uses sodium pyrosulfite-mediated hydrolysis of isothiouronium salts resulting from the reaction between N-protected aminoalkyl iodides and thiourea. N-Protected taurines were prepared through performic acid oxidation of the thiols and the products were further utilized for the synthesis of dipeptidosulfonamides. Georg Thieme Verlag Stuttgart - New York.
- Sureshbabu,Vishwanatha,Vasantha
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body text
p. 1037 - 1042
(2010/07/06)
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- Simple and efficient synthesis of Fmoc/Boc/Cbz-protected-β-amino alcohols and peptidyl alcohols employing Boc2O
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An efficient method for the activation of Fmoc/Boc/Cbz-protected amino acids using Boc2O and the reduction of the in situ generated carbonic-carbonic anhydride to their corresponding 1β-amino alcohols using sodium borohydride has been described. The method is simple, rapid and free from racemization. Besides, the protocol is also extended for the conversion of N-urethane protected peptide acids to their corresponding alcohols. Copyright
- Lalithamba,Sureshbabu, Vommina V.
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experimental part
p. 1372 - 1378
(2011/01/13)
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- Synthesis of peptide alcohols on the basis of an O-N acyl-transfer reaction
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(Figure Presented) Getting the better of troublemakers: C-terminal peptide alcohols cannot be synthesized by conventional solidphase peptide synthesis (SPPS) because of the absence of a free carboxylic group to attach to the resin. This problem was circumvented by anchoring a β-amino alcohol residue to the resin to provide a starting point for SPPS. An intramolecular O-N acyl shift completed the synthesis of the desired peptides (see scheme).
- Tailhades, Julien,Gidel, Marie-Aude,Grossi, Benjamin,Lecaillon, Jennifer,Brunel, Luc,Subra, Gilles,Martinez, Jean,Amblard, Muriel
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supporting information; experimental part
p. 117 - 120
(2010/04/04)
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- Tin(ii) chloride assisted synthesis of N-protected γ-amino β-keto esters through semipinacol rearrangement
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A facile synthetic route for the preparation of N-protected γ-amino β-keto esters from amino aldehydes and ethyl diazoacetate is described. The two component coupling is facilitated by tin(ii) chloride followed by semipinacol rearrangement leading to the product in quantitative yield. The reaction is mild, instantaneous and compatible with Boc-, Fmoc- and Cbz-amino protecting groups.
- Bandyopadhyay, Anupam,Agrawal, Neha,Mali, Sachitanand M.,Jadhav, Sandip V.,Gopi, Hosahudya N.
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supporting information; experimental part
p. 4855 - 4860
(2010/12/24)
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- Synthesis of thioureido-linked peptidomimetics, glycosylated amino acids, and neoglycoconjugates using bis(benzotriazolyl)methanethione as thioacylating agent
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A practical synthesis of thiourea-linked peptidomimetics, glycosylated amino acids, and neoglycoconjugates is described employing bis(benzotriazolyl) methanethione as thiocarbonylating reagent. The entire protocol is mild, efficient, high-yielding, and free from hazardous reagents. All the intermediates and products have been isolated and fully characterized by 1H NMR, 13C NMR, and mass spectrometry. Georg Thieme Verlag Stuttgart ? New York.
- Sureshbabu, Vommina V.,Chennakrishnareddy, Gundala,Hemantha, Hosahalli P.
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body text
p. 715 - 720
(2010/06/14)
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- N-urethane-protected amino alkyl isothiocyanates: Synthesis, isolation, characterization, and application to the synthesis of thioureidopeptides
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(Chemical Equation Presented) Synthetically useful N-Fmoc amino-alkyl isothiocyanates have been described, starting from protected amino acids. These compounds have been synthesized in excellent yields by thiocarbonylation of the monoprotected 1,2-diamines with CS2/TEA/p-TsCl, isolated as stable solids, and completely characterized. The procedure has been extended to the synthesis of amino alkyl isothiocyanates from Boc- and Z-protected amino acids as well. The utility of these isothiocyanates for peptidomimetics synthesis has been demonstrated by employing them in the preparation of a series of dithioureidopeptide esters. Boc-Gly-OH and Boc-Phe-OH derived isothiocyanates 9a and 9c have been obtained as single crystals and their structures solved through X-ray diffraction. They belong to the orthorhombic crystal system, and have a single molecule in the asymmetric unit (Z′ = 1). 9a crystallizes in the centrosymmetric space group Pbca, while 9c crystallizes in the noncentrosymmetric space group P212121.
- Sureshbabu, Vommina V.,Naik, Shankar A.,Hemantha,Narendra,Das, Ushati,Guru Row, Tayur N.
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supporting information; experimental part
p. 5260 - 5266
(2009/12/06)
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- Efficient synthesis of N-fmoc-aminoalkoxy pentafluorophenyl carbonates: Application for the synthesis of oligopeptidyl carbamates
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N-Fmoc-Aminoalkoxy pentafluorophenyl carbonates have been synthesized through the reaction of N-Fmoc-aminoalkoxy carbonyl chloride with pentafluorophenol. The reaction was clean and high yielding, and the products have been fully characterized using infra
- Sureshbabu, Vommina V.,Hemantha
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body text
p. 3555 - 3566
(2009/12/26)
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- Solid-phase synthesis of azidomethylene inhibitors targeting cysteine proteases
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An efficient strategy for the solid-phase synthesis of azidomethylene inhibitors targeting cysteine proteases is described. The method is highlighted by its compatibility with readily available building blocks, as well as its ability to accommodate differ
- Yang, Peng-Yu,Wu, Hao,Lee, Mei Yin,Xu, Ashley,Srinivasan, Rajavel,Yao, Shao Q.
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supporting information; experimental part
p. 1881 - 1884
(2009/04/18)
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- Synthesis of N-urethane protected β-amino alcohols employing N-(protected-α-aminoacyl)benzotriazoles
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A simple and racemisation-free synthesis of N-urethane protected α-amino/peptidyl alcohols by the reduction of the corresponding easily accessible N-acylbenzotriazoles is described. The method is practical, straightforward, fast and efficient for the synt
- Sureshbabu, Vommina V.,Sudarshan,Muralidhar,Narendra
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p. 683 - 685
(2008/09/20)
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- Reduction of pentafluorophenyl esters to the corresponding primary alcohols using sodium borohydride
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Primary alcohols and chiral N-protected 2-amino alcohols can be obtained in high yields from the reaction of pentafluorophenyl esters of the corresponding carboxylic acids with sodium borohydride in THF under mild conditions. This reductive method is rapid and compatible with various functional groups as well as with the most common N-protective groups Z, Boc and Fmoc.
- Papavassilopoulou, Eleni,Christofis, Petros,Terzoglou, Despina,Moutevelis-Minakakis, Panagiota
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p. 8323 - 8325
(2008/04/13)
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- Asymmetric synthesis of highly substituted azapolycyclic compounds via 2-alkenyl sulfoximines: Potential scaffolds for peptide mimetics
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The application of metalated, enantiomerically pure acyclic and cyclic 2-alkenyl sulfoximines for the synthesis of highly substituted aza(poly)cyclic ring systems is described. The method relies on a one-pot combination of a reagent-controlled allyl transfer reaction to α- or β-amino aldehydes, followed by a Michael-type cyclization of the intermediate vinyl sulfoximines generated in the first step. The sulfur-free target compounds are preferentially obtained by samarium iodide treatment of the sulfonimidoyl substituted heterocycles. In addition to this methodological work, initial results on the biological activity of selected examples are reported. Furthermore, a concept for the transformation of peptidic lead structures into non-peptide mimetics is described, and the relevance of the new approach to highly substituted azaheterocycles in this context is discussed.
- Reggelin, Michael,Junker, Bernd,Heinrich, Timo,Slavik, Stefan,Buehle, Philipp
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p. 4023 - 4034
(2007/10/03)
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- Synthesis of Fmoc-protected β-amino alcohols and peptidyl alcohols from Fmoc-amino acid/peptide acid azides
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An efficient synthesis of Nα-9H-fluoren-9- ylmethoxycarbony(Fmoc)-β-amino alcohols by the reduction of Fmoc-α-amino acyl azides employing aqueous NaBH4 as a reducing agent has been described. The reduction is found to be simple and almost complete. All the Fmoc-β-amino alcohols prepared are fully characterized by 1H and 13C NMR and mass spectrometry. Further, the method is extended for the reduction of seven Fmoc-dipeptidyl acids to the corresponding alcohols. Their reduction is also found to be smooth and complete.
- Babu, Vommina V. Suresh,Kantharaju,Sudarshan, Naremaddepalli S.
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p. 1880 - 1886
(2007/10/03)
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- Solid-phase synthesis of oligourea peptidomimetics employing the Fmoc protection strategy
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A solid-phase-Fmoc-based-synthesis strategy is described for oligourea peptidomimetics as well as a convenient general synthesis approach for the preparation of the required building blocks 5a-j and 5k. These are suitable for use in peptide or robot synthesizers, which is illustrated by the synthesis of oligourea peptidomimetics of part of Leu-enkephalin (10) and a neurotensin derivative (17).
- Boeijen,Van Ameijde,Liskamp
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p. 8454 - 8462
(2007/10/03)
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- An efficient synthesis of N-protected β-aminoethanesulfonyl chlorides: Versatile building blocks for the synthesis of oligopeptidosulfonamides
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A very efficient method for the synthesis of β-aminoethanesulfonyl chlorides is described. These aliphatic functionalized sulfonyl chlorides are accessible starting from a variety of protected amino acids, including those having functionalized side chains
- Brouwer,Monnee,Liskamp
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p. 1579 - 1584
(2007/10/03)
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- Synthesis of 9-fluorenylmethoxycarbonyl-protected amino aldehydes
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9-Fluorenylmethoxycarbonyl-protected amino aldehydes could be efficiently prepared in good yields by using two methods: (i) NaBH4 reduction of Fmoc-protected mixed anhydrides, followed by the Swern oxidation of the alcohols; and (ii) LiAlH
- Wen, James J.,Crews, Craig M.
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p. 1855 - 1858
(2007/10/03)
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- Selective one-pot conversion of carboxylic acids into alcohols
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Carboxylic acids are converted into alcohols by chemoselective reduction of their corresponding fluorides with sodium borohydride and dropwise addition of methanol. The method is general and mild and displays a high level of functional group compatibility. N-Protected amino and peptide alcohols, bearing varieties of protecting groups, are prepared in the same way from their corresponding amino acids and peptides without racemization.
- Kokotos, George,Noula, Caterina
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p. 6994 - 6996
(2007/10/03)
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- Synthesis of enantiopure N-and C-protected homo-β-amino acids by direct homologation of α-amino acids
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Enantiopure N-and/or C-protected homo-β-amino acids are prepared readily and in good yields from N-protected α-amino acids with the same side chain, via reduction of the carboxyl function and conversion of the resulting N-protected β-amino alcohol into the corresponding β-amino iodide and then β-amino cyanide. The key step of this strategy is represented by the synthesis of the enantiopure N-protected β-amino iodides 2 and 3 that are smoothly obtained from the parent amino alcohols 1 by polymer bound triarylphosphine-I2 complex in anhydrous dichloromethane.
- Caputo, Romualdo,Cassano, Ersilia,Longobardo, Luigi,Palumbo, Giovanni
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p. 12337 - 12350
(2007/10/02)
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- Chiral N-Protected β-Iodoamines from α-Aminoacids: a General Synthesis
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N-Protected D- or L-β-iodoamines (as 2), which are useful intermediates for the preparation of chiral β-aminoacids, are obtained smoothly from β-aminols (as 1) in two steps and high yields.
- Caputo, Romualdo,Cassano, Ersilia,Longobardo, Luigi,Palumbo, Giovanni
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p. 167 - 168
(2007/10/02)
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- Synthesis of Chiral N-Protected α-Amino Aldehydes by Reduction of N-Protected N-Carboxyanhydrides (UNCAs)
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A facile one step synthesis of a wide variety of N-protected (Boc, Z, Fmoc) α-amino aldehydes under mild conditions is described.Pure N-protected (Boc, Z, Fmoc) α-amino aldehydes were obtained in high yields by reduction of N-protected (Z, Boc, Fmoc)-N-ca
- Fehrentz, Jean-Alain,Pothion, Catherine,Califano, Jean-Christophe,Loffet, Albert,Martinez, Jean
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p. 9031 - 9034
(2007/10/02)
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- Synthesis of Chiral N-Protected β-Amino Alcohols by the Use of UNCAs
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A facile synthesis of a wide variety of N-protected β-amino alcohol derivatives under mild conditions is described.N-urethane protected amino acid N-carboxyanhydrides (UNCAs) were used as starting material and reduced into the corresponding alcohols with
- Fehrentz, Jean-Alain,Califano, Jean-Christophe,Amblard, Muriel,Loffet, Albert,Martinez, Jean
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p. 569 - 572
(2007/10/02)
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