Studies on Polypeptides. VIII. Synthesis of Peptides Related to Corticotropin<sup>1,2</sup>

Hofmann, Klaus; Jöhl, Albert; Furlenmeier, A.; Kappeler, H.

doi:10.1021/ja01564a030

Cited by 57 publications

(15 citation statements)

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“…The solution of Z-SM-Met was used directly for 13C NMR studies. Z-Methionine was prepared by the method of Hofmann et al 9 The Z dipeptide was prepared in the same manner from '---L-methionyl glycyl ethyl ester (Sigma, St. Louis, Mo. ).…”

Section: Methodsmentioning

confidence: 99%

Denaturation studies by carbon-13 nuclear magnetic resonance on modified basic pancreatic trypsin inhibitor using the novel S-[13C]methyl methionyl probe

Harina¹,

Dyckes²,

Willcott³

et al. 1980

J. Am. Chem. Soc.

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Section: Methodsmentioning

confidence: 99%

Denaturation studies by carbon-13 nuclear magnetic resonance on modified basic pancreatic trypsin inhibitor using the novel S-[13C]methyl methionyl probe

Harina¹,

Dyckes²,

Willcott³

et al. 1980

J. Am. Chem. Soc.

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“…Having reached the lasting blue end point, the excess of sodium and the sodium salts formed in the reduction are generally decomposed by addition of proton donors, e.g., acetic acid,134-136 ammonium chloride,20,30,94 ammonium iodide,47,55 ammonium sulfate,133 or ion-exchange resins. 93,137 In some cases no additives were provided. 132 There is no doubt that the addition of a proton donor is required at least for the decomposition of the sodium excess and sodium amide in order to prevent undesired side reactions and racemization (Section III).…”

Section: B the End Point And Duration Of The Reductionmentioning

confidence: 99%

Sodium-liquid ammonia reduction in peptide chemistry

Schön¹

1984

Chem. Rev.

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“…Preparation of Fragment C (Positions 24 -34). (Positions [33][34] Methyl Benzyloxycarbonylvalylglycinate. TEA (5.60 ml) was mixed with a stirred suspension of methyl glycinate hydrochloride (2.51 g) in THF (20 ml).…”

Section: Experimental Section25mentioning

confidence: 99%

Polypeptides. XLIX. Fragment condensations with peptide derivatives related to the primary structure of ribonuclease T1

Beacham¹,

Dupuis²,

Finn³

et al. 1971

J. Am. Chem. Soc.

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5526product mixtures were formed on irradiation. Small amounts of products with short retention times were observed, but these materials did not accumulate sufficiently to allow isolation. Addition of acetic acid after irradiation did not lead to any new product peaks.A preparative scale photolysis was carried out on 0.76 g of 17 in 100 ml of nitrogen-purged tert-butyl alcohol. After irradiation for 24 hr, the solvent was removed in vacuo and the residue was subjected to preparative gc (B, 180"). The major product (0.10 g) appeared to be a mixture of cyclobutanols as evidenced by the presence of hydroxyl absorptions in the infrared spectrum at 2.90 I J : nmr 6 1.21 ( s ) and 1.40 (s); mass spectrum mle (re1 intensities) 180 (1 I), 162 (38), 122 (loo), 43 (8 1). Abstract: Syntheses are described of three N-benzyloxycarbonylpeptide tert-butoxycarbonylhydrazides which correspond to positions 12-23, 24-34, and 3547, respectively, of the proposed primary structure of the enzyme ribonuclease TI. Evidence is presented to indicate that these materials are sequentially homogeneous. These fragments were condensed to form an N-benzyloxycarbonylhexatricontapeptide tert-butoxycarbonylhydrazide corresponding to positions 12-47 of the primary sequence of the enzyme. Available techniques to evaluate homogeneity of complex peptides are critically discussed and the concept of "diagnostic" amino acid residues is introduced.ibonuclease TI [ribonucleate guanine nucleotido-2'- Preparation of Fragments B, C, and DDoubly protected peptide hydrazides, such as fragments B, C, and D , are desirable intermediates for con-

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Studies on Polypeptides. VIII. Synthesis of Peptides Related to Corticotropin^1,2

Cited by 57 publications

References 1 publication

Denaturation studies by carbon-13 nuclear magnetic resonance on modified basic pancreatic trypsin inhibitor using the novel S-[13C]methyl methionyl probe

Denaturation studies by carbon-13 nuclear magnetic resonance on modified basic pancreatic trypsin inhibitor using the novel S-[13C]methyl methionyl probe

Sodium-liquid ammonia reduction in peptide chemistry

Polypeptides. XLIX. Fragment condensations with peptide derivatives related to the primary structure of ribonuclease T1

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Studies on Polypeptides. VIII. Synthesis of Peptides Related to Corticotropin1,2

Cited by 57 publications

References 1 publication

Denaturation studies by carbon-13 nuclear magnetic resonance on modified basic pancreatic trypsin inhibitor using the novel S-[13C]methyl methionyl probe

Denaturation studies by carbon-13 nuclear magnetic resonance on modified basic pancreatic trypsin inhibitor using the novel S-[13C]methyl methionyl probe

Sodium-liquid ammonia reduction in peptide chemistry

Polypeptides. XLIX. Fragment condensations with peptide derivatives related to the primary structure of ribonuclease T1

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Studies on Polypeptides. VIII. Synthesis of Peptides Related to Corticotropin^1,2