Darstellung geschützter peptid-fragmente unter einsatz substituierter triphenylmethyl-harze

Barlos, Kleomenis; Gatos, Dimitrios; Kallitsis, J. K.; Papaphotiu, Giorgos; Sotiriu, Petros; Yao, Wenqing; Schäfer, Wolfram

doi:10.1016/s0040-4039(00)99290-6

Cited by 323 publications

(179 citation statements)

References 12 publications

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“…The method is based on the principle that protected peptide fragments corresponding to the entire protein sequence can be condensed sequentially on a suitable solid support. We applied this method for the synthesis of MUC-1 oligomers using Fmoc amino acids and 2-chlorotrityl resin as the solid support (15).…”

Section: Resultsmentioning

confidence: 99%

“…This protection scheme allowed the mildest possible deprotection conditions of the final protected peptide. The solid support CLTR was chosen because it effectively suppresses diketopiperazin formation during the synthesis of peptides containing Pro (15)(16)(17) at the C terminus, and in addition the protected peptides synthesized on this resin could be cleaved quantitatively under extremely mild conditions in the absence of acids (18).…”

Section: Methodsmentioning

confidence: 99%

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Preparation of MUC-1 Oligomers Using an Improved Convergent Solid-phase Peptide Synthesis

Krambovitis¹,

Hatzidakis²,

Barlos³

1998

Journal of Biological Chemistry

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The sequentially repeating nature of the core mucin polypeptide chain MUC-1 on the surface of malignant cells makes it an excellent target for cancer immunotherapy. We describe a reliable and efficient method of synthesizing oligomers, up to five tandem repeats and oligomer heterotope derivatives with a 15-amino acid epitope from tetanus toxin using an improved convergent solid-phase peptide synthesis. The different oligomers were easily distinguishable by reverse-phase high pressure liquid chromatography, but they were poorly fixed and migrated with the same migration rate, irrespective of size, in electrophoretic studies. In contrast, the oligomer heterotopes exhibited size-dependent electrophoretic behavior but in high pressure liquid chromatography chromatograms the different heterotopes were eluted simultaneously in two peaks representing the L-and D-enantiomers of the derivatives. The oligomer heterotopes were recognized as antigens in Western blotting with a murine monoclonal antibody against the epitope APDTR. In enzyme immunoassay studies with the same antibody an increasing reactivity was observed against the larger oligomers and confirmed by inhibition assays as the MUC-1 pentamer was the most efficient inhibitor. These results support the suggestion that the pentamer attains a structure closer to the native conformation and is more immunogenic. In conclusion, large composite peptides can be reliably synthesized with the convergent solid-phase peptide strategy offering an attractive option to vaccine designing and development.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Preparation of MUC-1 Oligomers Using an Improved Convergent Solid-phase Peptide Synthesis

Krambovitis¹,

Hatzidakis²,

Barlos³

1998

Journal of Biological Chemistry

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“…the o-chlorotrityl group known to be cleaved under very mild acidic conditions. In addition, we decided to use its polymeric version, namely the o-chlorotrityl resin (PCTr), 8 in order to further improve its selectivity towards monoesterification. Indeed, treatment of PCTr-Cl resin (1.5 meq Cl/g resin) with fumaric acid in DMF in the presence of excess DIPEA at ambient temperature for overnight provided the polymeric monoester 18 (Scheme 2) with a calculated substitution of ca.…”

Section: Synthesis Of the Key-intermediate Anilide 13 And The Acitretmentioning

confidence: 99%

Synthetic studies towards the development of a novel class of acitretin-type retinoids

Magoulas¹,

Papaioannou²

2003

Arkivoc

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3,4,5-Trimethoxyaniline, indole-3-carboxylic acid and the dicarboxylic acids fumaric, maleic, succinic and phthalic have been combined to produce novel analogs of the aromatic retinoid acitretin. These analogs are characterized by a highly electron-rich benzene ring in the lipophilic part and two amide bonds, replacing the C7-C8 and C11-C12 double bonds, with simultaneous restriction of the C9-C10 double bond, in the spacer compared to acitretin. In addition, the terminal trans C13-C14 double bond has been either retained or isomerized or reduced or incorporated within an indole nucleus with simultaneous replacement of the carboxy group by the indole imine function. The related syntheses involved coupling of the N-Boc protected indole-3-carboxylic acid with 3,4,5-trimethoxyaniline, acid-mediated removal of the Boc group, coupling of the thus obtained anilide with the anhydrides or suitable monoesters of the above mentioned dicarboxylic acids in liquid or on solid phase and finally deprotection.

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“…8,11 Resin 1 can be cleaved even in the complete absence of acids with solutions of TFE or hexafluoroisopropanol. 30 Treatment with 1% trifluoroacetic acid (TFA) in DCM effects the cleavage of protected peptides from all resins 1-6.…”

Section: Solid Phase Synthesis Of Protected Segmentsmentioning

confidence: 99%

“…18 Resins and linkers of the trityl type have the additional advantage to suppress the piperazine formation at the dipeptide step of the synthesis. 8 This side reaction is especially pronounced in peptides, which contain Pro or Gly at their C-terminus. 31,32 Both of them are used very frequently in CPS as the C-terminal amino acid of the protected fragments.…”

Section: Solid Phase Synthesis Of Protected Segmentsmentioning

confidence: 99%

9-Fluorenylmethyloxycarbonyl/tbutyl-based convergent protein synthesis

Barlos

Gatos

1999

Biopolymers

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Besides linear solid phase peptide synthesis, segment condensation in solution and chemical ligation, convergent peptide synthesis (CPS) was developed in order to enable the efficient preparation of complex peptides and small proteins. According to this synthetic strategy, solid phase synthesized and suitably protected peptide fragments corresponding to the entire peptide/protein‐sequence are condensed on a solid support or in solution, to the target protein. This review summarizes CPS performed utilizing the mild 9‐fluorenylmethyloxycarbonyl/tbutyloxycarbonyl‐based protecting scheme for the amino acids. © 1999 John Wiley & Sons, Inc. Biopoly 51: 266–278, 1999

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Darstellung geschützter peptid-fragmente unter einsatz substituierter triphenylmethyl-harze

Cited by 323 publications

References 12 publications

Preparation of MUC-1 Oligomers Using an Improved Convergent Solid-phase Peptide Synthesis

Preparation of MUC-1 Oligomers Using an Improved Convergent Solid-phase Peptide Synthesis

Synthetic studies towards the development of a novel class of acitretin-type retinoids

9-Fluorenylmethyloxycarbonyl/tbutyl-based convergent protein synthesis

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