1,4-Diazepine-2,5-dione ring formation during solid phase synthesis of peptides containing aspartic acid β-benzyl ester

2007 ◽  
Vol 13 (11) ◽  
pp. 742-748 ◽  
Author(s):  
Helga Süli-Vargha ◽  
Gitta Schlosser ◽  
Janez Ilaš
Keyword(s):  
Aspartic Acid ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Benzyl Ester ◽  
Ring Formation ◽  
Phase Synthesis

Solid Phase Synthesis of Novel Fullerene Nucleotides Conjugates

2011 ◽  
Vol 266 ◽  
pp. 200-203
Author(s):  
Jing Zhang ◽  
Ya Dong Zhang
Keyword(s):  
Aspartic Acid ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Biological Properties ◽  
Azomethine Ylide ◽  
Hydroxyl Group ◽  
Spectrometric Analysis ◽  
Phase Synthesis ◽  
Chemical Structures ◽  
Controlled Pore Glass

N-substituted 3, 4-fullero pyrrolidine was synthesized according to 1, 3-dipolar cycloaddition of the azomethine ylide. Aspartic acid with protected α-amino and α-carboxyl groups was reacted with the activated hydroxyl group of N-substituted 3, 4-fullero pyrrolidine. The products were deprotected, affording the monofullerene aspartic acid (mFas). The conjugate FasT was synthesized by reaction of mFas containing protected amino group with the thymidylic acid derivatived controlled pore glass (CPG) using solid phase synthesis. All of the above fullerene derivatives were characterized by UV–vis, 1H NMR, IR and MS spectrometric analysis, giving the correct spectra with regard to their chemical structure. The chemical structures of fullerene nucleotides conjugate FasT is different from previous reports and may have novel biological properties. Moreover, they are more suitable for applications in biomedical research due to their solubilization in THF and DMSO. They have a potential to be used as monomer for the automatic synthesis. It allows further conjugation with specific biomolecules including amino acids, peptides, nucleotides and nucleic acids. A novel method has been developed to synthesize fullerene nucleotides conjugate. Their unique chemical structures make them very interesting for their potential use in medicine and biology.

Solid-phase synthesis of potential aspartic acid protease inhibitors containing a hydroxyethylamine isostere

1999 ◽  
Vol 40 (14) ◽  
pp. 2729-2732 ◽  
Author(s):  
Jinglan Zhou ◽  
Andreas Termin ◽  
Melissa Wayland ◽  
Christine M. Tarby
Keyword(s):  
Protease Inhibitors ◽  
Aspartic Acid ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Acid Protease ◽  
Phase Synthesis

Solid-phase synthesis of tailed cyclic peptides: The use of α-allyl-protected aspartic acid leads to aspartimide and tetramethylguanidinium formation

1996 ◽  
Vol 3 (2) ◽  
pp. 89-97 ◽  
Author(s):  
Dominique Delforge ◽  
Marc Dieu ◽  
Edouard Delaive ◽  
Muriel Art ◽  
Barbara Gillon ◽  
...  
Keyword(s):  
Aspartic Acid ◽  
Cyclic Peptides ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis

Modification of Oligopeptides on Aspartic Acid or Lysine Residues by Solid-Phase Synthesis through On-Resin Side-Chain Conjugation

Synlett ◽  
2018 ◽  
Vol 29 (19) ◽  
pp. 2588-2594
Author(s):  
Hongyan Shen ◽  
Xibo Ning ◽  
Di Liu ◽  
Shimiao Liu ◽  
Mingjie Zhang
Keyword(s):  
Aspartic Acid ◽  
Potential Application ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Practical Method ◽  
Protecting Groups ◽  
Side Chain ◽  
Phase Synthesis ◽  
Lysine Residues

On-resin side-chain conjugations of various moieties to oligo­peptides were performed through an orthogonal protecting protocol using side-chain-protecting groups for aspartic acid or lysine that could be selectively removed on-resin. Various types of modification, such as PEGylation, biotinylation, glycosylation, or fluorophore-labeling of peptides, were realized by using this strategy. The formation of ester, amide, hydrazide, and thiourea bonds was accomplished through the on-resin conjugation. Our work provides an improved and convenient solid-phase synthetic protocol for the modification of oligopeptides on their aspartic acid or lysine residues. This is a universal and practical method that is expected to increase the potential application of peptide-related drugs.

Solid-phase synthesis of caged peptides containing photolabile derivatives of aspartic acid

2002 ◽  
pp. 656-657
Author(s):  
Yoshiro Tatsu ◽  
Yasushi Shigeri ◽  
Shinji Sogabe ◽  
Noboru Yumoto ◽  
Susumu Yoshikawa
Keyword(s):  
Aspartic Acid ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis ◽  
Derivatives Of
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