Studies on polypeptides XXXIX. The role of the imidazole <i>tele</i>‐nitrogen atom of histidine‐12 in the catalytic action of RNase S′

Hoes, C.J.T.; Kerling, K. E. T.; Havinga, E.

doi:10.1002/recl.19831020304

Cited by 6 publications

(2 citation statements)

References 68 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Boc-Leu-D Z 3Pal azlactone (7) Boc-Leu-dl-Ser(3Pyr)-OH (5) (3.0 g, 7.59 mmol) and sodium acetate (761 mg, 8 mmol) were dissolved in acetic anhydride (10 mL) and the solution was stirred for 4 h at room temperature. The reaction mixture was concentrated in vacuo and the residue was extracted with ethyl acetate.…”

Section: General Proceduresmentioning

confidence: 99%

“…Recently, preliminary reports indicated that a helical octapeptide possessing two (b-3-pyridyl)-l-Ala (3Pal) residues as metal ion-binding amino acids can form a 1 : 1 complex with Co 2+ (5). In addition, 3Pal is a useful amino acid to explore structure-activity relationship (SAR) of biologically active peptides (6)(7)(8)(9)(10)(11). We considered that Fig.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis, crystal structure and molecular conformation of N^α‐Boc‐l‐leucyl‐(Z)‐β‐(3‐pyridyl)‐α,β‐ dehydroalanyl‐l‐leucine methyl ester*

Yamada

Oku

Shinoda

et al. 2005

The Journal of Peptide Research

View full text Add to dashboard Cite

show abstract

Section: General Proceduresmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis, crystal structure and molecular conformation of N^α‐Boc‐l‐leucyl‐(Z)‐β‐(3‐pyridyl)‐α,β‐ dehydroalanyl‐l‐leucine methyl ester*

Yamada

Oku

Shinoda

et al. 2005

The Journal of Peptide Research

View full text Add to dashboard Cite

show abstract

Studies on intramolecular hydrogen bonding between the pyridine nitrogen and the amide hydrogen of the peptide: synthesis and conformational analysis of tripeptides containing novel amino acids with a pyridine ring

et al. 2005

View full text Add to dashboard Cite

For the first time tripeptides, Z-AA(1)-Xaa-AA(3)-OMe (AA(1) and AA(3) = Gly or Aib, Xaa = 2Pmg and 2Pyg) were prepared containing alpha-methyl-alpha-(2-pyridyl)glycine (2Pmg) and alpha-(2-pyridyl)glycine (2Pyg) by solid-phase Ugi reaction. These results clearly indicate that for the preparation of tripeptides containing an amino acid with a pyridine ring, the solid-phase Ugi reaction is very useful.NMR analysis clarified that 2Pmg-containing tripeptides adopt a unique conformation with an intramolecular hydrogen bond between 2Pmg-NH and the pyridine nitrogen. However, in the case of Z-Gly-2Pyg-Gly-OMe, the intramolecular hydrogen bonding between 2Pyg-NH and the pyridine nitrogen was not observed, whereas Z-Aib-2Pyg-Aib-OMe adopts a unique conformation with an intramolecular hydrogen bond between 2Pyg-NH and a pyridine nitrogen. Conformational analysis of the tripeptides, Z-AA(1)-Xaa-AA(3)-OMe (AA(1), AA(3) = Gly or Aib, Xaa = alpha,alpha-di(2-pyridyl)glycine (2Dpy), alpha-phenyl-alpha-(2-pyridyl)glycine (2Ppg), 2Pmg and 2Pyg), clarified that when an alpha,alpha-disubstituted glycine with a 2-pyridyl group at an alpha-carbon atom is introduced into any peptide, an intramolecular hydrogen bond between a pyridine nitrogen and an amide proton is formed and conformational mobility of the peptide backbone is restricted.

show abstract

Studies on polypeptides XL. The role of histidine‐119 in non‐covalent semisynthetic ribonuclease; its replacement by 3‐(3‐pyrazolyl)‐L‐alanine, N^π‐methyl‐L‐histidine and N^τ‐methyl‐L‐histidine

Serdijn

Bloemhoff

Kerling

et al. 1984

Recl. Trav. Chim. Pays‐Bas

View full text Add to dashboard Cite

50J . Serdijn et a/. / Studies on polypeptides c m -' . The polymer derived from 4d was isolated by adding the concentrated reaction mixture to an excess of ether/acetone (lO/l, v/v). The polymer was deprotected using sodium in liquid ammonk3, submitted to ultrafiltration and freeze-dried. The HCI salt of the product thus obtained had the same physical properties as described above. Prepmution of fhc nickel cornplesesNickel(I1) complexes of isocyanides were prepared at -3OoC by rapid addition of a 0.02 mol/l solution of Ni(C10,),.6Hz0 in ethanol/ether (1/1 v/v) to a vigorously stirred 0.25 mol/l solution of the appropriate isocyanide in the same solvent. The complexes precipitated instantaneously and were collected by centrifugation, after which they were washed once with ethanol/ether (1/4 v/v) and three times with ether. They were dried in vucuo over P,O, at 4OOC.. Relevant physical data are summarized in Table 11. AcknowledgementThis research was supported by the Netherlands Foundation for Chemical Research (SON) with financial aid from the Netherlands Organization for the Advancement of Pure Research (ZWO).Recl. Trav. Chim. Pays-Bas 103, 50-54 (1984) 0034 - Abstract. Non-covalent semisynthetic ribonuclease analogues are used to study the role of histidine-I 19 in the active site of RNase A. The solid-phase synthesis of three RNase I 1 1-124 peptides, in which histidine-I 19 is replaced by 3-(3-pyrazolyl)-~-alanine, N"-methyl-L-histidine and N'-methyl-L-histidine, respectively, is described. The binding of these peptides to RNase 1-1 I8 protein is examined. The enzymatic activities of the resulting complexes towards first and second step substrates and their binding to the inhibitor 3'-cytidine monophosphate are determined. The N"-methylhistidine-and the 3-(3-pyrazolyl)alanine RNase analogues are devoid of catalytic activity. The W-methylhistidine analogue is found to be enzymatically active, using yeast ribonucleic acid and 2',3'-CMP as substrates. With the latter substrate, kinetic parameters at pH 6.0 have been determined. The results provide strong evidence to suggest that the pros-nitrogen atom of His-1 19 plays an essential role as acid/base catalyst in the enzymatic reaction of RNase. There are indications that the tele-nitrogen atom of histidine-I 19 in the natural enzyme -besides effecting the right pK value at the pros-nitrogen centre -may also contribute by favouring the optimal steric orientation of the imidazole nucleus and of the pros-nitrogen in particular.

show abstract

Studies on polypeptides XXXIX. The role of the imidazole tele‐nitrogen atom of histidine‐12 in the catalytic action of RNase S′

Abstract: Abstract. Of three analogues of des(l5-20)-RNase S

Cited by 6 publications

References 68 publications

Synthesis, crystal structure and molecular conformation of N^α‐Boc‐l‐leucyl‐(Z)‐β‐(3‐pyridyl)‐α,β‐ dehydroalanyl‐l‐leucine methyl ester*

Synthesis, crystal structure and molecular conformation of N^α‐Boc‐l‐leucyl‐(Z)‐β‐(3‐pyridyl)‐α,β‐ dehydroalanyl‐l‐leucine methyl ester*

Studies on intramolecular hydrogen bonding between the pyridine nitrogen and the amide hydrogen of the peptide: synthesis and conformational analysis of tripeptides containing novel amino acids with a pyridine ring

Studies on polypeptides XL. The role of histidine‐119 in non‐covalent semisynthetic ribonuclease; its replacement by 3‐(3‐pyrazolyl)‐L‐alanine, N^π‐methyl‐L‐histidine and N^τ‐methyl‐L‐histidine

Contact Info

Product

Resources

About

Studies on polypeptides XXXIX. The role of the imidazole tele‐nitrogen atom of histidine‐12 in the catalytic action of RNase S′

Abstract: Abstract. Of three analogues of des(l5-20)-RNase S

Cited by 6 publications

References 68 publications

Synthesis, crystal structure and molecular conformation of Nα‐Boc‐l‐leucyl‐(Z)‐β‐(3‐pyridyl)‐α,β‐ dehydroalanyl‐l‐leucine methyl ester*

Synthesis, crystal structure and molecular conformation of Nα‐Boc‐l‐leucyl‐(Z)‐β‐(3‐pyridyl)‐α,β‐ dehydroalanyl‐l‐leucine methyl ester*

Studies on intramolecular hydrogen bonding between the pyridine nitrogen and the amide hydrogen of the peptide: synthesis and conformational analysis of tripeptides containing novel amino acids with a pyridine ring

Studies on polypeptides XL. The role of histidine‐119 in non‐covalent semisynthetic ribonuclease; its replacement by 3‐(3‐pyrazolyl)‐L‐alanine, Nπ‐methyl‐L‐histidine and Nτ‐methyl‐L‐histidine

Contact Info

Product

Resources

About

Synthesis, crystal structure and molecular conformation of N^α‐Boc‐l‐leucyl‐(Z)‐β‐(3‐pyridyl)‐α,β‐ dehydroalanyl‐l‐leucine methyl ester*

Synthesis, crystal structure and molecular conformation of N^α‐Boc‐l‐leucyl‐(Z)‐β‐(3‐pyridyl)‐α,β‐ dehydroalanyl‐l‐leucine methyl ester*

Studies on polypeptides XL. The role of histidine‐119 in non‐covalent semisynthetic ribonuclease; its replacement by 3‐(3‐pyrazolyl)‐L‐alanine, N^π‐methyl‐L‐histidine and N^τ‐methyl‐L‐histidine