Synthesis of oligophosphopeptides and related ATP .gamma.-peptide esters as probes for cAMP-dependent protein kinase

Johnson, Thomas; Coward, James K.

doi:10.1021/jo00385a023

Cited by 26 publications

(7 citation statements)

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“…GlcNAcB (1,4/ the method of Johnson and Coward (1987) was used for the conjugation of carboxylic acid and amino groups. An example of this method will be described under Results.…”

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confidence: 99%

Binding characteristics of N-acetylglucosamine-specific lectin of the isolated chicken hepatocytes: similarities to mammalian hepatic galactose/N-acetylgalactosamine-specific lectin

Lee¹,

Rice²,

Rao³

et al. 1989

Biochemistry

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Binding characteristics of N-acetylglucosamine- (GlcNAc) specific lectin on the chicken hepatocyte surface were probed by an inhibition assay using various sugars and glycosides as inhibitors. Results indicated that the binding area of the lectin is small, interacting only with GlcNAc residues whose 3- and 4-OH's are open. The combining site is probably of trough-type, since substitution with as large a group as monosaccharide is permitted on the C-6 side of GlcNAc, and on the C-1 side, the aglycon of GlcNAc can be very large (e.g., a glycoprotein). These binding characteristics are shared with the homologous mammalian lectin specific for galactose/N-acetylgalactosamine, suggesting that tertiary structure of the combining area of these two lectins is similar. This is understandable, since there is approximately 40% amino acid sequence identity in the carbohydrate recognition domain of these two lectins [Drickamer, K., Mannon, J. F., Binns, G., & Leung, J. O. (1984) J. Biol. Chem. 259, 770-778]. A series of glycosides, each containing two GlcNAc residues separated by different distances (from 0.8 to 4.7 nm), were synthesized. Inhibition assay with these and other cluster glycosides indicated that clustering of two or more GlcNAc residues increased the affinity toward the chicken lectin tremendously. Among the ligands containing two GlcNAc residues, the structure which allows a maximal inter-GlcNAc distance of 3.3 nm had the strongest affinity, its affinity increase over GlcNAc (monosaccharide) amounting to 100-fold. Longer distances slightly diminished the affinity, while shortening the distance caused substantial decrease in the affinity.(ABSTRACT TRUNCATED AT 250 WORDS)

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“…GlcNAcB (1,4/ the method of Johnson and Coward (1987) was used for the conjugation of carboxylic acid and amino groups. An example of this method will be described under Results.…”

mentioning

confidence: 99%

Binding characteristics of N-acetylglucosamine-specific lectin of the isolated chicken hepatocytes: similarities to mammalian hepatic galactose/N-acetylgalactosamine-specific lectin

Lee¹,

Rice²,

Rao³

et al. 1989

Biochemistry

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“…In contrast, ATP analogs modified with phosphoester moieties are very stable and therefore well‐suited to studying enzymatic activity (Hacker et al., ). Classically, these molecules are synthesized by coupling a monophosphate and a diphosphate to give the triphosphate modified at both ends (e.g., Johnson and Coward, ; Lee et al., ). While this method reliably results in the expected nucleotides, two phosphorylated species have to be prepared before the coupling step and especially the synthesis of a modified diphosphate is regularly a challenging task.…”

Section: Commentarymentioning

confidence: 99%

Synthesis of γ‐Phosphate‐Labeled and Doubly Labeled Adenosine Triphosphate Analogs

Hacker

Welter

Marx

2015

CP Nucleic Acid Chemistry

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This unit describes the synthesis of γ-phosphate-labeled and doubly labeled adenosine triphosphate (ATP) analogs and their characterization using the phosphodiesterase I from Crotalus adamanteus (snake venom phosphodiesterase; SVPD). In the key step of the synthesis, ATP or an ATP analog, bearing a linker containing a trifluoroacetamide group attached to the nucleoside, are modified with an azide-containing linker at the terminal phosphate using an alkylation reaction. Subsequently, different labels are introduced to the linkers by transformation of one functional group to an amine and coupling to an N-hydroxysuccinimide ester. Specifically, the Staudinger reaction of the azide is employed as a straightforward means to obtain an amine in the presence of various labels. Furthermore, the fluorescence characteristics of a fluorogenic, doubly labeled ATP analog are investigated following enzymatic cleavage by SVPD.

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“…A phosphorylated heptapeptide was synthesized in an interesting way [85]. First the C-terminal tripeptide (H-SerLeu-Gly-R HCl) was prepared and phosphorylated through the use of diphenylphosphochloridate.…”

Section: 'Global' Approachmentioning

confidence: 99%

Phosphopeptides - Chemical Synthesis, Analysis, Outlook and Limitations.

Tóth¹,

Kele²,

Váradi³

2007

COC

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Protein phosphorylation is one of the most important post-translational events in cell regulation and signal transduction. Since the isolation of phosphorylated peptides from biological sources is usually not feasible, there is a need for efficient chemical phosphorylation methods to allow the study of the role of phosphorylation/dephosphorylation in biological processes. The recent developments in phosphopeptide chemistry (special protecting groups for the phosphate moiety and new amidite reagents) have provided peptide chemists with a wide variety of different strategies applicable for work with the sensitive phosphoserine, phosphothreonine and phosphotyrosine-containing peptides. This has made possible the efficient chemical preparation of longer, multiply phosphorylated, possibly cell-permeable or fluorescent residue-bearing peptides.

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Synthesis of oligophosphopeptides and related ATP .gamma.-peptide esters as probes for cAMP-dependent protein kinase

Cited by 26 publications

References 5 publications

Binding characteristics of N-acetylglucosamine-specific lectin of the isolated chicken hepatocytes: similarities to mammalian hepatic galactose/N-acetylgalactosamine-specific lectin

Binding characteristics of N-acetylglucosamine-specific lectin of the isolated chicken hepatocytes: similarities to mammalian hepatic galactose/N-acetylgalactosamine-specific lectin

Synthesis of γ‐Phosphate‐Labeled and Doubly Labeled Adenosine Triphosphate Analogs

Phosphopeptides - Chemical Synthesis, Analysis, Outlook and Limitations.

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