Synthesis of polymeric N-hydroxysuccinimide esters of N-substituted amino acids and peptides

1975 ◽  
Vol 24 (2) ◽  
pp. 356-360
Author(s):  
S. V. Rogozhin ◽  
Yu. A. Davidovich ◽  
N. A. Samoilova ◽  
N. V. Mironova ◽  
A. I. Yurtanov ◽  
...  
Keyword(s):  
Amino Acids ◽  
Hydroxysuccinimide Esters

ChemInform Abstract: SYNTHESIS OF POLY-N-HYDROXYSUCCINIMIDE ESTERS OF N-PROTECTED AMINO ACIDS AND PEPTIDES

1975 ◽  
Vol 6 (26) ◽  
pp. no-no
Author(s):  
S. V. ROGOZHIN ◽  
YU. A. DAVIDOVICH ◽  
N. A. SAMOILOVA ◽  
N. V. MIRONOVA ◽  
A. I. YURTANOV ◽  
...  
Keyword(s):  
Amino Acids ◽  
Hydroxysuccinimide Esters

The Use of Free Amino Acids and Peptides as Amino Components in Reactions with PolymericN-Hydroxysuccinimide Esters

Synthesis ◽  
1977 ◽  
Vol 1977 (05) ◽  
pp. 303-304 ◽  
Author(s):  
S. M. ANDREEV ◽  
V. A. TSIRYAPKIN ◽  
N. A. SAMOILOVA ◽  
N. V. MIRONOVA ◽  
Yu. A. DAVIDOVICH ◽  
...  
Keyword(s):  
Amino Acids ◽  
Free Amino Acids ◽  
Free Amino ◽  
Hydroxysuccinimide Esters

scholarly journals A novel high-yield synthesis of aminoacyl p-nitroanilines and aminoacyl 7-amino-4-methylcoumarins: Important synthons for the synthesis of chromogenic/fluorogenic protease substrates

2011 ◽  
Vol 7 ◽  
pp. 1030-1035 ◽  
Author(s):  
Xinghua Wu ◽  
Yu Chen ◽  
Herve Aloysius ◽  
Longqin Hu
Keyword(s):  
Amino Acids ◽  
High Yield ◽  
Easy Access ◽  
General Applicability ◽  
Peptide Substrates ◽  
Peptide Chemistry ◽  
Amino Acid Peptide ◽  
Hydroxysuccinimide Esters ◽  
Fluorogenic Peptide

Aminoacyl p-nitroaniline (aminoacyl-pNA) and aminoacyl 7-amino-4-methylcoumarin (aminoacyl-AMC) are important synthons for the synthesis of chromogenic/fluorogenic protease substrates. A new efficient method was developed to synthesize aminoacyl-pNA and aminoacyl-AMC derivatives in excellent yields starting from either amino acids or their corresponding commercially available N-hydroxysuccinimide esters. The method involved the in situ formation of selenocarboxylate intermediate of protected amino acids and the subsequent non-nucleophilic amidation with an azide. Common protecting groups used in amino acid/peptide chemistry were all well-tolerated. The method was also successfully applied to the synthesis of a dipeptide conjugate, indicating that the methodology is applicable to the synthesis of chromogenic substrates containing short peptides. The method has general applicability to the synthesis of chromogenic and fluorogenic peptide substrates and represents a convenient and high-yield synthesis of N α-protected-aminoacyl-pNAs/AMCs, providing easy access to these important synthons for the construction of chromogenic/fluorogenic protease substrates through fragment condensation or stepwise elongation.

ChemInform Abstract: THE USE OF FREE AMINO ACIDS AND PEPTIDES AS AMINO COMPONENTS IN REACTIONS WITH POLYMERIC N-HYDROXYSUCCINIMIDE ESTERS

1977 ◽  
Vol 8 (35) ◽  
pp. no-no
Author(s):  
S. M. ANDREEV ◽  
V. A. TSIRYAPKIN ◽  
N. A. SAMOILOVA ◽  
N. V. MIRONOVA ◽  
YU. A. DAVIDOVICH ◽  
...  
Keyword(s):  
Amino Acids ◽  
Free Amino Acids ◽  
Free Amino ◽  
Hydroxysuccinimide Esters

Succinimidyl esters of fatty acids for amino acid acylations

1976 ◽  
Vol 54 (5) ◽  
pp. 733-737 ◽  
Author(s):  
Alenka Paquet
Keyword(s):  
Amino Acids ◽  
Fatty Acids ◽  
Amino Acid ◽  
Free Amino ◽  
Side Chain ◽  
Amino Acid Esters ◽  
Amino Group ◽  
Acyl Chlorides ◽  
Hydroxysuccinimide Esters ◽  
Acid Esters

Fatty acid N-hydroxysuccinimide esters have been prepared from the thallium(I) salt of N-hydroxysuccinimide and the corresponding acyl chlorides in essentially quantitative yields. These active esters were used for acylation of amino acid esters in organic solvents, or of free amino acids in aqueous medium. The title compounds were found to be selective towards the side chain amino group of lysine. An efficient preparation of ε-N-benzyloxycarbonyl-L-lysine using benzyl succinimidyl carbonate is described.

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