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An peptide antibiotic was isolated from one of the nastiest looking bacteria ever viewed. The following observations were made about the peptide. a) Acid hydrolysis yielded equimolar amounts of the following: leu, orn, phe, pro and val. Ornithine (orn) is an amino acid not found in proteins, but is found in peptides. We will see it later when we discuss the Urea Cycle. It has the structure HN-CH,-CH:-CH,--co0 "NH, b) For what it is worth, the molecular weight of the peptide is about 1200. c) When treated with the enzyme carboxypeptidase, an enzyme which degrades peptides from the carboxyterminus, the peptide failed to undergo hydrolysis.( Whoa, we are not in Kansas anymore, Toto!) d) Treatment with fluorodinitrobenzene, which will react with N-terminal amino acids, followed by acid hydrolysis yielded unmodified amino acids and the following derivative of ornithine. Please note where the orn is modified. e) Partial hydrolysis followed by chromatographic separation yielded the following di- and tri- peptides: leu-phe phe-pro orn-leu val-orn val-orn-leu phe-pro-val pro-val-orn Given the above information, determine the amino acid sequence of the peptide.

An peptide antibiotic was isolated from one of the nastiest looking bacteria ever viewed. The following observations were made about the peptide. a) Acid hydrolysis yielded equimolar amounts of the following: leu, orn, phe, pro and val. Ornithine (orn) is an amino acid not found in proteins, but is found in peptides. We will see it later when we discuss the Urea Cycle. It has the structure HN-CH,-CH:-CH,--co0 "NH, b) For what it is worth, the molecular weight of the peptide is about 1200. c) When treated with the enzyme carboxypeptidase, an enzyme which degrades peptides from the carboxyterminus, the peptide failed to undergo hydrolysis.( Whoa, we are not in Kansas anymore, Toto!) d) Treatment with fluorodinitrobenzene, which will react with N-terminal amino acids, followed by acid hydrolysis yielded unmodified amino acids and the following derivative of ornithine. Please note where the orn is modified. e) Partial hydrolysis followed by chromatographic separation yielded the following di- and tri- peptides: leu-phe phe-pro orn-leu val-orn val-orn-leu phe-pro-val pro-val-orn Given the above information, determine the amino acid sequence of the peptide.

Biochemistry
Biochemistry
9th Edition
ISBN:9781319114671
Author:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Publisher:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Chapter1: Biochemistry: An Evolving Science
Section: Chapter Questions
Problem 1P
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An peptide antibiotic was isolated from one of the nastiest looking bacteria ever viewed. The following observations were made about the peptide. a) Acid hydrolysis yielded equimolar amounts of the following: leu, orn, phe, pro and val. Ornithine (orn) is an amino acid not found in proteins, but is found in peptides. We will see it later when we discuss the Urea Cycle. It has the structure HN-CH,-CH:-CH,--co0 "NH, b) For what it is worth, the molecular weight of the peptide is about 1200. c) When treated with the enzyme carboxypeptidase, an enzyme which degrades peptides from the carboxyterminus, the peptide failed to undergo hydrolysis.( Whoa, we are not in Kansas anymore, Toto!) d) Treatment with fluorodinitrobenzene, which will react with N-terminal amino acids, followed by acid hydrolysis yielded unmodified amino acids and the following derivative of ornithine. Please note where the orn is modified. e) Partial hydrolysis followed by chromatographic separation yielded the following di- and tri- peptides: leu-phe phe-pro orn-leu val-orn val-orn-leu phe-pro-val pro-val-orn Given the above information, determine the amino acid sequence of the peptide.
Transcribed Image Text:An peptide antibiotic was isolated from one of the nastiest looking bacteria ever viewed. The following observations were made about the peptide. a) Acid hydrolysis yielded equimolar amounts of the following: leu, orn, phe, pro and val. Ornithine (orn) is an amino acid not found in proteins, but is found in peptides. We will see it later when we discuss the Urea Cycle. It has the structure HN-CH,-CH:-CH,--co0 "NH, b) For what it is worth, the molecular weight of the peptide is about 1200. c) When treated with the enzyme carboxypeptidase, an enzyme which degrades peptides from the carboxyterminus, the peptide failed to undergo hydrolysis.( Whoa, we are not in Kansas anymore, Toto!) d) Treatment with fluorodinitrobenzene, which will react with N-terminal amino acids, followed by acid hydrolysis yielded unmodified amino acids and the following derivative of ornithine. Please note where the orn is modified. e) Partial hydrolysis followed by chromatographic separation yielded the following di- and tri- peptides: leu-phe phe-pro orn-leu val-orn val-orn-leu phe-pro-val pro-val-orn Given the above information, determine the amino acid sequence of the peptide.
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