IUPAC-IUB commission on biochemical nomenclature. Symbols for amino-acid derivatives and peptides. Recommendations (1971)

Ltd, Portland Press

doi:10.1042/bj1260773

Cited by 37 publications

(2 citation statements)

References 7 publications

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“…Abbreviations used for amino acids and designation of peptides follow the rules of the IUPAC-IUB Commission of Biochemical Nomenclature in IUPAC-IUB Commission on Biochemical Nomenclature. 40 Amino acid symbols denote the L-configuration unless indicated otherwise. Abbreviated nomenclature for cyclic peptides followed the rules of the application by Albericio et al 41 "&" indicated the bridging points in the cyclic peptide.…”

Section: Notesmentioning

confidence: 99%

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Extended Solution-phase Peptide Synthesis Strategy Using Isostearyl-Mixed Anhydride Coupling and a New C-Terminal Silyl Ester-Protecting Group for N-Methylated Cyclic Peptide Production

Nagaya

Murase

Mimori

et al. 2021

Org. Process Res. Dev.

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Herein, we present a new and efficient convergent solution-phase synthetic strategy for producing peptides containing N-methyl amino acids. Specifically, we have synthesized a model cyclic octapeptide with two N-methyl amino acids, utilizing an isostearyl-mixed anhydride coupling methodology and a novel silyl ester-protecting group, cyclohexyl di-tert-butyl silyl (cHBS). This newly developed method uses an isostearic acid chloride (ISTA-Cl) and silylation reagent that allows coupling between N-and Cterminally unprotected amino acids with sterically hindered N-methyl amino acids. High yields of four dipeptide fragments are efficiently synthesized by omitting the traditional C-terminal deprotection step. The silyl ester-protecting group at the C-terminus is stable during general peptide synthesis, and is selectively cleaved by fluoride ions. This group further suppresses diketopiperazine formation during the deprotection of the N α -amino-protecting group. The linear octapeptide precursor is convergently synthesized utilizing protection and selective deprotection of the silyl ester-protecting group, and the cyclic octapeptide can be obtained with high purity using this novel methodology, via a route shorter than conventional solution-phase peptide synthesis strategies.

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Section: Notesmentioning

confidence: 99%

mentioning

confidence: 99%

Extended Solution-phase Peptide Synthesis Strategy Using Isostearyl-Mixed Anhydride Coupling and a New C-Terminal Silyl Ester-Protecting Group for N-Methylated Cyclic Peptide Production

Nagaya

Murase

Mimori

et al. 2021

Org. Process Res. Dev.

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Conformation of dioxopiperazines. III. Conformational‐energy calculations and evaluation of specific forces contributing to the intramolecular dioxopiperazine‐phenyl ring‐ring folding in cyclo(glycyl‐phenylalanyl)

Kołodziejczyk

Ciarkowski

1986

Biopolymers

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SynopsisConformational energy calculations on cyclo(glycy1-L-phenylalanyl, c(G1y-Phe), were carried out by means of the semiempirical MO CNDO/2 method. They corroborated earlier experimental findings that in c(G1y-Phe) the conformations with a n aromatic sidechain ring folded over the dioxopiperazine (DOP) ring contribute significantly to the overall equilibrium, provided that the empirical optimization of the DOP ring geometry, extracted from x-ray data, rather than that of the CNDOIZderived data is used throughout the computations. Following these studies, more detailed calculations, based partly on CNDOIZderived data and partly on experimental data, were carried out to clarify the question, which are the forces responsible for this ring-ring stacking? In contrast to early suggestions, it was found that the quadrupole-quadrupole and dispersion interactions mainly contribute to folded conformations of c(G1y-Phe). Some implications of this finding on devising force fields for molecular-mechanics calculations of peptides are briefly outlined.

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Conformation of dioxopiperazines, II. CNDO/2 quantum mechanical calculations on conformational preferences in cyclo (glycyl‐L‐alanyl), cyclo(glycyl‐L‐valyl), and both epimers of cyclo‐di‐(alanyl)

Bielinski¹,

Ciarkowski²

1986

Biopolymers

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SynopsisConformational energy calculations, aimed at verification of the suitability of the semiempirical molecular orbital CND0/2 method for conformational elucidations in cyclic dipeptides formed from amino acids with aliphatic side chains, have been carried, and both epimers of cycbdi-(Alanyl)] point out very good agreement with experimental premises. The latter include (1) the preference of the cis-peptide bonds for being nonplanar, which results in twisted-boat conformations of the DOP ring; (2) greater stability of conformers with a side chain oriented axially over those with a side chain oriented equatorially; (3) the preference of cycZo(G1y-Val) for assuming a folded conformation with one of the side chain y-methyl groups sticking over the DOP ring.

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IUPAC-IUB commission on biochemical nomenclature. Symbols for amino-acid derivatives and peptides. Recommendations (1971)

Cited by 37 publications

References 7 publications

Extended Solution-phase Peptide Synthesis Strategy Using Isostearyl-Mixed Anhydride Coupling and a New C-Terminal Silyl Ester-Protecting Group for N-Methylated Cyclic Peptide Production

Extended Solution-phase Peptide Synthesis Strategy Using Isostearyl-Mixed Anhydride Coupling and a New C-Terminal Silyl Ester-Protecting Group for N-Methylated Cyclic Peptide Production

Conformation of dioxopiperazines. III. Conformational‐energy calculations and evaluation of specific forces contributing to the intramolecular dioxopiperazine‐phenyl ring‐ring folding in cyclo(glycyl‐phenylalanyl)

Conformation of dioxopiperazines, II. CNDO/2 quantum mechanical calculations on conformational preferences in cyclo (glycyl‐L‐alanyl), cyclo(glycyl‐L‐valyl), and both epimers of cyclo‐di‐(alanyl)

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