cas 160885-98-3, FMOC-L-VALINOL | Articles data

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Copper-Free Huisgen Cycloaddition for the 14-3-3-Templated Synthesis of Fusicoccin-Peptide Conjugates
Mid-sized molecules have emerged as an attractive chemical space and potentially provide a robust basis for the development of synthetic agents to control intracellular protein interactions. However, the limited cell permeability and chemical tractability of such agents remain to be addressed. We envisioned that target-templated synthesis of such mid-sized molecules might provide a solution. Here, we exploited a copper-free Huisgen cycloaddition for template synthesis using a peptide fragment containing a 4,8-diazacyclononyne (DACN) moiety and an azide-containing fusicoccin derivative in the presence or absence of recombinant 14-3-3ζ protein in vitro. Time-course changes in the yield of products demonstrated that the reaction was accelerated in the presence of 14-3-3 and one of the regioisomers was generated predominantly, supporting the template effect.
Masuda, Ryoma,Kawasaki, Yuuya,Igawa, Kazunobu,Manabe, Yoshiyuki,Fujii, Hiroshi,Kato, Nobuo,Tomooka, Katsuhiko,Ohkanda, Junko
p. 742 - 747
(2020)
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Distinct Lugdunins from a New Efficient Synthesis and Broad Exploitation of Its MRSA-Antimicrobial Structure
A new solid-phase peptide synthesis and bioprofiling of the antimicrobial activity of lugdunin, a fibupeptide, enable a comprehensive structure-activity relationship (SAR) study (MRSA Staphylococcus aureus). Distinct lugdunin analogues with variation of the three important amino acids Val2, Trp3, and Leu4 are readily available based on the established high-output synthesis. This efficient synthesis concept takes advantage of the presynthesized thiazolidine building block. To gain further knowledge of SAR, d-Val2, and d-Leu4 were replaced with aliphatic amino acids. For l-Trp3 derivatization, a set of non-natural aromatic amino acids with manifold substitution and annulation patterns precisely shows structural imperatives, starting from the exchange of d-Val6 → d-Trp6 with a 2-fold improved biological activity. d-Trp6-lugdunin analogues with additional variation of d-Val2 and d-Leu4 residues were designed and synthesized followed by antimicrobial profiling. For the first time, these SAR studies deliver valuable information on the tolerance of other amino acids to d-Val2, l-Trp3, and d-Leu4 in the sequence of lugdunin.
Saur, Julian S.,Wirtz, Sebastian N.,Schilling, Nadine A.,Krismer, Bernhard,Peschel, Andreas,Grond, Stephanie
p. 4034 - 4058
(2021/05/04)

O-Alkyl S-(Pyridin-2-yl)carbonothiolates: Operationally Simple and Highly Nitrogen-Selective Reagents for Alkoxy Carbonylation of Amino Groups
Amino groups are selectively protected in good yields by reaction with O-Alkyl S-(pyridin-2-yl)carbonothiolates in an appropriate solvent at room temperature in air. Even glucosamine, which contains multiple hydroxyl groups, is selectively N-protected in methanol.
Hashimoto, Yoshimitsu,Morita, Nobuyoshi,Suzuki, Tomoyuki,Tamura, Osamu,Tanaka, Kosaku
p. 899 - 902
(2020/05/28)

Synthetic Lugdunin Analogues Reveal Essential Structural Motifs for Antimicrobial Action and Proton Translocation Capability
Lugdunin, a novel thiazolidine cyclopeptide, exhibits micromolar activity against methicillin-resistant Staphylococcus aureus (MRSA). For structure–activity relationship (SAR) studies, synthetic analogues obtained from alanine and stereo scanning as well as peptides with modified thiazolidine rings were tested for antimicrobial activity. The thiazolidine ring and the alternating d- and l-amino acid backbone are essential. Notably, the non-natural enantiomer displays equal activity, thus indicating the absence of a chiral target. The antibacterial activity strongly correlates with dissipation of the membrane potential in S. aureus. Lugdunin equalizes pH gradients in artificial membrane vesicles, thereby maintaining membrane integrity, which demonstrates that proton translocation is the mode of action (MoA). The incorporation of extra tryptophan or propargyl moieties further expands the diversity of this class of thiazolidine cyclopeptides.
Schilling, Nadine A.,Berscheid, Anne,Schumacher, Johannes,Saur, Julian S.,Konnerth, Martin C.,Wirtz, Sebastian N.,Beltrán-Bele?a, José M.,Zipperer, Alexander,Krismer, Bernhard,Peschel, Andreas,Kalbacher, Hubert,Br?tz-Oesterhelt, Heike,Steinem, Claudia,Grond, Stephanie
supporting information
p. 9234 - 9238
(2019/07/16)

Staudinger/aza-Wittig reaction to access Nβ-protected amino alkyl isothiocyanates
A unified approach to access Nβ-protected amino alkyl isothiocyanates using Nβ-protected amino alkyl azides through a general strategy of Staudinger/aza-Wittig reaction is described. The type of protocol used to access isothiocyanates depends on the availability of precursors and also, especially in the amino acid chemistry, on the behavior of other labile groups towards the reagents used in the protocols; fortunately, we were not concerned about both these factors as precursor-azides were prepared easily by standard protocols, and the present protocol can pave the way for accessing title compounds without affecting Boc, Cbz and Fmoc protecting groups, and benzyl and tertiary butyl groups in the side chains. The present strategy eliminates the need for the use of amines to obtain title compounds and thus, this method is step-economical; additional advantages include retention of chirality, convenient handling and easy purification. A few hitherto unreported compounds were also prepared, and all final compounds were completely characterized by IR, mass, optical rotation, and 1H and 13C NMR studies.
Santhosh,Durgamma,Shekharappa,Sureshbabu, Vommina V.
p. 4874 - 4880
(2018/07/15)

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
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
p. 131 - 136
(2017/04/24)

A greener, efficient and catalyst-free ultrasonic-assisted protocol for the n-fmoc protection of amines
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
p. 546 - 550
(2016/03/19)

Solvent-free reduction of carboxylic acids to alcohols with NaBH4 promoted by 2,4,6-trichloro-1,3,5-triazine and PPh3 in the presence of K2CO3
A simple, rapid, and eco-friendly method for NaBH4 reduction of carboxylic acids to alcohols under solvent-free conditions was developed using a combination of 2,4,6-trichloro-1,3,5-triazine (TCT) with a catalytic amount of triphenylphosphine as an acid activator. With the 1 : 0.2 : 1.5 : 2 mole ratio of TCT : PPh3 : K2CO3 : NaBH4, carboxylic acids including aromatic acids, aliphatic acids, and N-protected α-amino acids (Fmoc, Z) could readily undergo reduction to give the corresponding alcohols in good to excellent yields within 10 min.
Jaita, Subin,Kaewkum, Pantitra,Duangkamol, Chuthamat,Phakhodee, Wong,Pattarawarapan, Mookda
p. 46947 - 46950
(2014/12/10)

An expedient route for the reduction of carboxylic acids to alcohols employing 1-propanephosphonic acid cyclic anhydride as acid activator
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.
experimental part
p. 5059 - 5063
(2012/09/22)

A facile synthesis and crystallographic analysis of N-protected β-amino alcohols and short peptaibols
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.
supporting information; experimental part
p. 4182 - 4187
(2011/06/28)

Synthesis and biological evaluation of novel irreversible serine protease inhibitors using amino acid based sulfonyl fluorides as an electrophilic trap
We have designed and synthesized novel irreversible serine protease inhibitors containing aliphatic sulfonyl fluorides as an electrophilic trap. These substituted taurine sulfonyl fluorides derived from taurine or protected amino acids were conveniently s
Brouwer, Arwin J.,Ceylan, Tarik,Jonker, Anika M.,Linden, Tima Van Der,Liskamp, Rob M.J.
p. 2397 - 2406
(2011/05/12)

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
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
body text
p. 1037 - 1042
(2010/07/06)

Simple and efficient synthesis of Fmoc/Boc/Cbz-protected-β-amino alcohols and peptidyl alcohols employing Boc2O
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.
experimental part
p. 1372 - 1378
(2011/01/13)

N-urethane-protected amino alkyl isothiocyanates: Synthesis, isolation, characterization, and application to the synthesis of thioureidopeptides
(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.
supporting information; experimental part
p. 5260 - 5266
(2009/12/06)

Efficient synthesis of N-fmoc-aminoalkoxy pentafluorophenyl carbonates: Application for the synthesis of oligopeptidyl carbamates
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
body text
p. 3555 - 3566
(2009/12/26)

Synthesis of β-aminoethanesulfonyl fluorides or 2-substituted taurine sulfonyl fluorides as potential protease inhibitors
Substituted taurine sulfonyl fluorides derived from taurine or protected amino acids are conveniently synthesized from β-aminoethanesulfonyl chlorides using KF/18-crown-6 or from β-aminoethanesulfonates using DAST.
Brouwer, Arwin J.,Ceylan, Tarik,Linden, Tima van der,Liskamp, Rob M.J.
scheme or table
p. 3391 - 3393
(2009/09/05)

Synthesis of Fmoc-protected β-amino alcohols and peptidyl alcohols from Fmoc-amino acid/peptide acid azides
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.
p. 1880 - 1886
(2007/10/03)

Synthesis and applications of β-aminoethanesulfonyl azides
A very efficient method for the synthesis of β-aminoethanesulfonyl azides is descibed. These aliphatic sulfonyl azides are accessible starting from a variety of protected amino acids, including those having functionalized side chains. Furthermore, these s
Brouwer, Arwin J.,Merkx, Remco,Dabrowska, Katarzyna,Rijkers, Dirk T. S.,Liskamp, Rob M. J.
p. 455 - 460
(2007/10/03)

Highly Stereoselective Conversion of Aryl Peptidyl Ketones into the Corresponding Peptide Alcohols
In this paper we describe the conversion of aryl peptidyl ketones, by a hydride reduction, into the corresponding peptide alcohols. The developed methodology is highly stereoselective and represents a very important application in peptide chemistry for obtaining peptide alcohols. It provides peptide alcohols with definite stereochemistry and in moderate, but satisfactory, yields. The reducing procedure, performed with NaBH3CN and TiCl4, probably proceeds via two diastereomeric cyclic intermediates that show different reactivity. The stereochemistry of the resulting alcohols was established after obtaining them by an alternative synthetic procedure. Furthermore, the methodology adopted keeps the urethane protecting group on the amino function of the N-terminal amino acid residue. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
Di Gioia, Maria Luisa,Leggio, Antonella,Le Pera, Adolfo,Liguori, Angelo,Siciliano, Carlo
p. 463 - 467
(2007/10/03)

Solid-phase synthesis of oligourea peptidomimetics employing the Fmoc protection strategy
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
p. 8454 - 8462
(2007/10/03)

A practical solid phase synthesis of oligopeptidosulfonamide foldamers
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
p. 7991 - 7995
(2007/10/03)

An efficient synthesis of N-protected β-aminoethanesulfonyl chlorides: Versatile building blocks for the synthesis of oligopeptidosulfonamides
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
p. 1579 - 1584
(2007/10/03)

Mild reduction of carboxylic acids to alcohols using cyanuric chloride and sodium borohydride
Several carboxylic acids, including N-Boc, N-Cbz and N-Fmoc amino acids were reduced to the corresponding alcohols by activation of the carboxy function with cyanuric chloride and N-methylmorpholine followed by reduction with aqueous sodium borohydride.
Falorni, Massimo,Porcheddu, Andrea,Taddei, Maurizio
p. 4395 - 4396
(2007/10/03)

Synthesis of 9-fluorenylmethoxycarbonyl-protected amino aldehydes
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.
p. 1855 - 1858
(2007/10/03)

Stepwise Automated Solid Phase Synthesis of Naturally Occurring Peptaibols Using FMOC Amino Acid Fluorides
The standard methods of stepwise solid phase synthesis according to Merrifield could not previously be applied to the synthesis of the important naturally occurring peptaibols because of difficulties arising from the pronounced steric hindrance caused by α,α-dialkylated amino acids (incomplete coupling, especially to adjacent similarly constituted units, racemization due to slow coupling to hindered amino acids, etc.), chain degradation due to the presence of acid-labile Aib-Pro linkages, and the lack of any general method for the loading of C-terminal amino alcohols to resin supports.Following recent work on model systems, it is now shown that the adoption of Fmoc amino acid fluorides as coupling reagents makes possible the facile, general assembly of such peptides.The method was demonstrated for alamethicin F30 and F50, saturnisporin SA III, and trichotoxin A50J.The crude products were of remarkable purity.Amino acid analysis, mass spectral data, and comparison of the synthetic alamethicins with samples of naturally occurring material confirmed the success of the syntheses.No significant amount of racemization (0.8percent) was found for any of the chiral amino acids present.The first step of the synthesis involved a new general method for assembly of C-terminal peptide alcohols via the use of o-chlorotrityl resin.In addition, model studies on the question of racemization during the coupling of Fmoc amino acid fluorides are reported.
Wenschuh, Holger,Beyermann, Michael,Haber, Hanka,Seydel, Joachim K.,Krause, Eberhard,et al.
p. 405 - 410
(2007/10/02)