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Volumn 13, Issue 7, 2012, Pages 987-991

Use of a Multicomponent Reaction for Chemoselective Derivatization of Multiple Classes of Metabolites

Author keywords

Biomarkers; Isocyanide; Metabolites; Metabolomics; Ugi reaction

Indexed keywords

ALDEHYDE; ALPHA AMINO ACID; AMINE; CARBOXYLIC ACID; FATTY ACID DERIVATIVE; GLUTAMINE; HISTIDINE; KETONE DERIVATIVE; NEUROTRANSMITTER; PHENYLALANINE; POLYAMINE DERIVATIVE;

EID: 84860248519     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.201200035     Document Type: Article
Times cited : (12)

References (25)
  • 19
    • 84870723193 scopus 로고    scopus 로고
    • In reactions of aspartic acid and glutamic acid, the α-amino acid moieties participate in a Ugi 4-component 5-center reaction, while the carboxylate side chain participated in a Passerini reaction. This is a so-called tandem Ugi-Passerini reaction.
    • In reactions of aspartic acid and glutamic acid, the α-amino acid moieties participate in a Ugi 4-component 5-center reaction, while the carboxylate side chain participated in a Passerini reaction. This is a so-called tandem Ugi-Passerini reaction.
  • 20
    • 84870723917 scopus 로고    scopus 로고
    • Except for reactions with tryptophan, tyrosine and serine, our yields are higher than those reported by Ugi. In the aforementioned cases, Ugi included triethylamine presumably to enhance the nucleophilicity of methanol. These findings imply that these reactions need not be performed at -30°C.
    • Except for reactions with tryptophan, tyrosine and serine, our yields are higher than those reported by Ugi. In the aforementioned cases, Ugi included triethylamine presumably to enhance the nucleophilicity of methanol. These findings imply that these reactions need not be performed at -30°C.
  • 21
    • 84870667898 scopus 로고    scopus 로고
    • Note
    • Arginine's basic guanidinium group facilitates solvolytic cleavage of the isocyanide carbamate, yielding a methyl carbamate. The poor solubility of cysteine in methanol and acetonitrile precludes efficient reaction.
  • 22
    • 84870694562 scopus 로고    scopus 로고
    • Note
    • Benzylamine, 4-pentenoic acid, and/or isobutyraldehyde were selected for use as the other U-4CR substrates in these derivatization experiments.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.