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Fmoc amino acids

Similarly, chiral nitrones (61a—c) and (62a—c) were obtained from the corresponding a-amino aldehydes (209, 210), nitrones (63a,b) from p-amino-a-hydroxy aldehydes (211), and chiral nitrones (64) and (65) from IV-fluorenyl-methoxycarbonyl (/V-Fmoc) amino acids and /V-Fmoc-dipeptides (Fig. 2.6) (212). [Pg.155]

Y = O-Linked amino acid glycosides Z = /V-a-FMoc-amino acid glycosides... [Pg.89]

Owing to steric hindrance, the acylation reaction must be carried out using a large excess (4-10 Eq.) of the activated acid and for an extended period. In some cases, repeat acylation is recommended. Acylation has also been successfully carried out using Fmoc-amino acid fluorides (e.g., Fmoc-Phe-F4, 4Eq. in the presence of DIEA, 1.1 Eq. 18h >98% acylation efficiency). While acylation with unhindered activated carboxylic acids are achieved in >98%, acylation with hindered carboxylic acids generally resulted in ca. 80% efficiencies. [Pg.96]

With the C-terminal residue introduced as part of the BAL anchor and the penultimate residue incorporated successfully by the optimized acylation conditions just described, further stepwise chain elongation by addition of Fmoc-amino acids generally proceeded normally by any of a variety of peptide synthesis protocols. [Pg.136]

Fmoc-amino acid, TBTU/HOBt, DIEA, DMF... [Pg.270]

Both FMOC and its hydrolysis products have similar absorption and fluorescence spectra to FMOC-amino acids. Excess FMOC remaining after derivatization reacts with water to form 9-fluorenylmethyl alcohol (FMOC-OH), and if this is not removed prior to sample injection, it elutes as a large, broad peak in the vicinity of proline. [Pg.54]

FMOC-amino acids can be chromatographed using a C8 column and acetonitrile in sodium acetate buffer as the mobile phase. Fluorescence detection with excitation at 260nm and emission at 31 Onm gives the best results. [Pg.54]

FMOC Amino acid FMOC-amino acid Simplified reaction between FMOC and amino acids... [Pg.54]

FIGURE 2.14 Peptide-bond formation from chlorides of A-alkoxycarbonylamino acids. N-9-Fluorenylmethoxycarbonylamino-acid chlorides.41 The base is NaHCO, Na2C03, or a tertiary amine. The reaction is carried out in a one- or two-phase system. The latter is used to try to suppress formation of the 2-alkoxy-5(4//)-oxazolone that is generated by the action of the base on the acid chloride. The method is applicable primarily to Fmoc-amino-acid derivatives that do not have acid-sensitive protecting groups on their side chains. [Pg.43]

S Pass, B Amit, A Parchomik. Racemization-free photochemical coupling of peptide segments. (Fmoc-amino-acid chlorides) J Am Chem Soc 103, 7674, 1981. [Pg.44]

LA Carpino, BJ Cohen, KE Stephens, SY Sadat-Aalaee, J-H Tien, DC Lakgridge. (9-Fluorenylmethyl)oxycarbonyl (Fmoc) amino acid chlorides. Synthesis, characterization, and application to the rapid synthesis of short peptide segments. J Org Chem 51, 3732, 1986... [Pg.44]

A recently described approach involving zinc dust for eliminating acid allows acylation by 9-fluorenylmethoxycarbonyl chloride without dimer formation. The amino acid is dissolved in acetonitrile with the aid of hydrochloric acid, and zinc dust is added to destroy the acid and deprotonate the zwitter-ion, reducing the protons to gaseous hydrogen (Figure 3.16). Acylation is effected in the presence of zinc dust, which reduces the proton that is liberated by the reaction as soon it is formed. See Section 7.7 for another possible impurity in Fmoc amino acids.34,36-39... [Pg.81]

PBW Ten Koortenaar, BG Van Dijk, JM Peeters, BJ Raaben, PJH Adams, GI Tesser. Rapid and efficient method for preparation of Fmoc-amino acids starting from 9-fluorenylmethanol. Int J Pept Prot Res 27, 398, 1986. [Pg.81]

HN Gopi, VV Suresh Babu. Zinc-promoted simple synthesis of oligomer-free N -Fmoc-amino acids using Fmoc-Cl as an acylating agent under neutral conditions. J Pept Res 55, 295, 2000. [Pg.81]

D Granitza, M Beyermann, H Wenschuh, H Haber, LA Carpino, GA Truran, M Bienert. Efficient acylation of hydroxy functions by means of Fmoc amino acid fluorides. J Chem Soc Chem Commun 2223, 1995. [Pg.116]

ESTERIFICATION OF FMOC-AMINO ACIDS TO HYDROXYMETHYL GROUPS OF SUPPORTS... [Pg.151]

During the first decade when solid-phase synthesis was executed using Fmoc/tBu chemistry, the first Fmoc-amino acid was anchored to the support by reaction of the symmetrical anhydride with the hydroxymethylphenyl group of the linker or support. Because this is an esterification reaction that does not occur readily, 4-dimethylaminopyridine was employed as catalyst. The basic catalyst caused up to 6% enantiomerization of the activated residue (see Section 4.19). Diminution of the amount of catalyst to one-tenth of an equivalent (Figure 5.21, A) reduced the isomerization substantially but did not suppress it completely. As a consequence, the products synthesized during that decade were usually contaminated with a small amount of the epimer. In addition, the basic catalyst was responsible for a second side reaction namely, the premature removal of Fmoc protector, which led to loading of some dimer of the first residue. Nothing could be done about the situation,... [Pg.151]

FIGURE 5.21 Methods for anchoring an Fmoc-amino acid to the hydroxymethyl group of a linker-resin. (A) 4-Dimethylaminopyridine-catalyzed acylation by the symmetrical anhydride.19 (B) Acylation by a mixed anhydride obtained from 2,6-dichlorobenzoyl chloride.39 (C) Acylation by the acid fluoride.50 (D) Dicyclohexylcarbodiimide-mediated acylation in the presence of 1-hydroxybenzotriazole.52... [Pg.151]

An alternative to the above is esterification by reaction of the salt of the Fmoc-amino acid with the halomethylphenyl-support (see Section 3.17). It was established in the 1960s that this method of esterifying A-alkoxycarbonylamino acids, which does not involve electrophilic activation, is not accompanied by enan-tiomerization. Examples of supports with haloalkyl linkers are bromomethylphe-noxymethyl-polystyrene and 2-chlorotrityl chloride resin (see Section 5.23). [Pg.152]

A Grandas, X Jorba, E Giralt, E Pedroso. Anchoring of Fmoc-amino acids to hydroxymethyl resins. Int J Pept Prot Res 33, 386, 1987. [Pg.152]

FIGURE 5.22 (A) Reaction of an Fmoc-amino acid with 2-chlorotrityl chloride resin.56 The ester bond formed is cleavable by the mild acid, which does not affect tert-butyl-based protectors. (B) Generation of a protected peptide containing cystine by detachment of a chain, deprotection of cysteine residues, and oxidation of the sulfhydryls by the reagent containing iodine. The cations produced are trapped by CF3CH2OH. [Pg.153]

K Barlos, O Chatzi, D Gatos, G Stavropoulus. 2-Chlorotrityl chloride resin. Studies on anchoring of Fmoc-amino acids and peptide cleavage. Int J Pept Prot Res 37,513,... [Pg.154]


See other pages where Fmoc amino acids is mentioned: [Pg.73]    [Pg.75]    [Pg.203]    [Pg.91]    [Pg.297]    [Pg.543]    [Pg.89]    [Pg.25]    [Pg.70]    [Pg.136]    [Pg.265]    [Pg.271]    [Pg.272]    [Pg.294]    [Pg.294]    [Pg.297]    [Pg.300]    [Pg.15]    [Pg.43]    [Pg.80]    [Pg.114]    [Pg.116]    [Pg.141]    [Pg.152]    [Pg.152]    [Pg.153]    [Pg.164]    [Pg.202]   
See also in sourсe #XX -- [ Pg.13 , Pg.129 ]




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Fmoc, amino acid protection with

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Fmoc-protected amino acids

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