Studies on the substrate specificity of a peptide amidase partially purified from orange flavedo. 1993

D Kammermeier-Steinke, and A Schwarz, and C Wandrey, and M R Kula
Institut für Enzymtechnologie, Universität Düsseldorf, Germany.

We recently reported the isolation and some properties of an unusual enzyme called peptide amidase (Steinke, D. and Kula, M. R. Angew. Chem. Int. Ed. Engl. 1990, 29, 1139-1140). Here we describe the partial purification of the enzyme from the flavedo of orange fruits and discuss results of a detailed study of the substrate range of the peptide amidase, which is extremely wide and useful for a C-terminal enzymatic deprotection in peptide synthesis under very mild conditions. The substrate spectrum includes protected or unprotected peptide amides and N-protected amino acid amides. The chain length of the substrate peptide amide, as well as the amino acid composition, including the C-terminal amino acid side chain, are of minor importance. The peptide amidase is stereoselective with regard to the C-terminal position, since only L-amino acid amides are accepted as substrates, with the exception of proline. Notably, side chain amides are not deamidated. The peptide amidase is free of any proteolytic activity, which would hydrolyze internal peptide bonds of substrate peptides. In the penultimate position D-amino acids are tolerated; peptide modifications toward the N-terminal region do not abolish the enzymatic deamidation at the C-terminus.

UI MeSH Term Description Entries
D008969 Molecular Sequence Data Descriptions of specific amino acid, carbohydrate, or nucleotide sequences which have appeared in the published literature and/or are deposited in and maintained by databanks such as GENBANK, European Molecular Biology Laboratory (EMBL), National Biomedical Research Foundation (NBRF), or other sequence repositories. Sequence Data, Molecular,Molecular Sequencing Data,Data, Molecular Sequence,Data, Molecular Sequencing,Sequencing Data, Molecular
D010455 Peptides Members of the class of compounds composed of AMINO ACIDS joined together by peptide bonds between adjacent amino acids into linear, branched or cyclical structures. OLIGOPEPTIDES are composed of approximately 2-12 amino acids. Polypeptides are composed of approximately 13 or more amino acids. PROTEINS are considered to be larger versions of peptides that can form into complex structures such as ENZYMES and RECEPTORS. Peptide,Polypeptide,Polypeptides
D002240 Carbohydrate Sequence The sequence of carbohydrates within POLYSACCHARIDES; GLYCOPROTEINS; and GLYCOLIPIDS. Carbohydrate Sequences,Sequence, Carbohydrate,Sequences, Carbohydrate
D002957 Citrus A plant genus of the family RUTACEAE. They bear the familiar citrus fruits including oranges, grapefruit, lemons, and limes. There are many hybrids which makes the nomenclature confusing. Citron Tree,Fruit, Citrus,Lemon Tree,Orange Tree, Bitter,Orange Tree, Mandarin,Orange Tree, Seville,Orange Tree, Sour,Pomelo Tree,Pummelo Tree,Tangerine Tree,Citrus Fruit,Citrus aurantium,Citrus bergamia,Citrus grandis,Citrus hystrix,Citrus limon,Citrus maxima,Citrus medica,Citrus reticulata,Kaffir Lime,Bitter Orange Tree,Bitter Orange Trees,Citron Trees,Citrus aurantiums,Citrus bergamias,Citrus grandi,Citrus hystrices,Citrus medicas,Citrus reticulatas,Lemon Trees,Lime, Kaffir,Mandarin Orange Tree,Mandarin Orange Trees,Orange Trees, Bitter,Orange Trees, Mandarin,Orange Trees, Seville,Orange Trees, Sour,Pomelo Trees,Pummelo Trees,Seville Orange Tree,Seville Orange Trees,Sour Orange Tree,Sour Orange Trees,Tangerine Trees,Tree, Bitter Orange,Tree, Citron,Tree, Lemon,Tree, Mandarin Orange,Tree, Pomelo,Tree, Pummelo,Tree, Seville Orange,Tree, Sour Orange,Tree, Tangerine,Trees, Bitter Orange,Trees, Citron,Trees, Lemon,Trees, Mandarin Orange,Trees, Pomelo,Trees, Pummelo,Trees, Seville Orange,Trees, Sour Orange,Trees, Tangerine,aurantium, Citrus,bergamia, Citrus,hystrices, Citrus,maxima, Citrus,medicas, Citrus,reticulata, Citrus
D000581 Amidohydrolases Any member of the class of enzymes that catalyze the cleavage of amide bonds and result in the addition of water to the resulting molecules. Amidases,Amidohydrolase
D000595 Amino Acid Sequence The order of amino acids as they occur in a polypeptide chain. This is referred to as the primary structure of proteins. It is of fundamental importance in determining PROTEIN CONFORMATION. Protein Structure, Primary,Amino Acid Sequences,Sequence, Amino Acid,Sequences, Amino Acid,Primary Protein Structure,Primary Protein Structures,Protein Structures, Primary,Structure, Primary Protein,Structures, Primary Protein
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D013373 Substance P An eleven-amino acid neurotransmitter that appears in both the central and peripheral nervous systems. It is involved in transmission of PAIN, causes rapid contractions of the gastrointestinal smooth muscle, and modulates inflammatory and immune responses. Euler-Gaddum Substance P,Hypothalamic Substance P,SP(1-11),Euler Gaddum Substance P,Substance P, Euler-Gaddum,Substance P, Hypothalamic
D013379 Substrate Specificity A characteristic feature of enzyme activity in relation to the kind of substrate on which the enzyme or catalytic molecule reacts. Specificities, Substrate,Specificity, Substrate,Substrate Specificities

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