Org Lett. 2002 Aug 22;4(17):2865-8.

General method for the synthesis of caged phosphopeptides: tools for the exploration of signal transduction pathways.

Rothman DM, Vázquez ME, Vogel EM, Imperiali B.

Source

Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, USA.

Abstract

[reaction: see text] An interassembly approach for the synthesis of peptides containing 1-(2-nitrophenyl)ethyl-caged phosphoserine, -threonine, and -tyrosine has been developed. Photochemical uncaging of these peptides releases the 2-nitrophenylethyl protecting group to afford the corresponding phosphopeptide. The peptides described herein are based on phosphorylation sites of kinases involved in cell movement or cell cycle regulation and demonstrate the versatility of the method and compatibility with the synthesis of polypeptides, including a variety of encoded amino acids.

PMID:: 12182575; [PubMed - indexed for MEDLINE]

Publication Types, MeSH Terms, Substances, Grant Support

Publication Types

MeSH Terms

Substances

Grant Support

LinkOut - more resources

Full Text Sources

Other Literature Sources

COS Scholar Universe

Supplemental Content

Save items

Related citations in PubMed

Sequential activation and deactivation of protein function using spectrally differentiated caged phosphoamino acids. [J Am Chem Soc. 2011]
Sequential activation and deactivation of protein function using spectrally differentiated caged phosphoamino acids.
Goguen BN, Aemissegger A, Imperiali B. J Am Chem Soc. 2011 Jul 27; 133(29):11038-41. Epub 2011 Jun 29.
A new approach to phosphoserine, phosphothreonine and phosphotyrosine synthons and to thiophospho analogs. Stepwise synthesis of mono- and multiphosphorylated phosphopeptides related to src-protein kinase. [Int J Pept Protein Res. 1995]
A new approach to phosphoserine, phosphothreonine and phosphotyrosine synthons and to thiophospho analogs. Stepwise synthesis of mono- and multiphosphorylated phosphopeptides related to src-protein kinase.
Mora N, Lacombe JM, Pavia AA. Int J Pept Protein Res. 1995 Jan; 45(1):53-63.
Caged phospho-amino acid building blocks for solid-phase peptide synthesis. [J Org Chem. 2003]
Caged phospho-amino acid building blocks for solid-phase peptide synthesis.
Rothman DM, Vazquez ME, Vogel EM, Imperiali B. J Org Chem. 2003 Aug 22; 68(17):6795-8.
Review [Development of new deprotecting methodologies for peptides and application to studies on signaling mechanism]. [Yakugaku Zasshi. 2000]
Review [Development of new deprotecting methodologies for peptides and application to studies on signaling mechanism].
Otaka A. Yakugaku Zasshi. 2000 Jan; 120(1):54-67.
Review Quantitative proteomic approaches for studying phosphotyrosine signaling. [Expert Rev Proteomics. 2007]
Review Quantitative proteomic approaches for studying phosphotyrosine signaling.
Ding SJ, Qian WJ, Smith RD. Expert Rev Proteomics. 2007 Feb; 4(1):13-23.

See reviews... See all...

Cited by 4 PubMed Central articles

NCAD, a database integrating the intrinsic conformational preferences of non-coded amino acids. [J Phys Chem B. 2010]
NCAD, a database integrating the intrinsic conformational preferences of non-coded amino acids.
Revilla-López G, Torras J, Curcó D, Casanovas J, Calaza MI, Zanuy D, Jiménez AI, Cativiela C, Nussinov R, Grodzinski P, et al. J Phys Chem B. 2010 Jun 3; 114(21):7413-22.
Caged O-phosphorothioyl amino acids as building blocks for Fmoc-based solid phase peptide synthesis. [Tetrahedron. 2007]
Caged O-phosphorothioyl amino acids as building blocks for Fmoc-based solid phase peptide synthesis.
Aemissegger A, Carrigan CN, Imperiali B. Tetrahedron. 2007 Jul 2; 63(27):6185-6190.
Review Illuminating the chemistry of life: design, synthesis, and applications of "caged" and related photoresponsive compounds. [ACS Chem Biol. 2009]
Review Illuminating the chemistry of life: design, synthesis, and applications of "caged" and related photoresponsive compounds.
Lee HM, Larson DR, Lawrence DS. ACS Chem Biol. 2009 Jun 19; 4(6):409-27.

See all...

Related information

Related Citations
Calculated set of PubMed citations closely related to the selected article(s) retrieved using a word weight algorithm. Related articles are displayed in ranked order from most to least relevant, with the “linked from” citation displayed first.
Compound (MeSH Keyword)
PubChem chemical compound records that are classified under the same Medical Subject Headings (MeSH) controlled vocabulary as the current articles.
Substance (MeSH Keyword)
PubChem chemical substance (submitted) records that are classified under the same Medical Subject Headings (MeSH) controlled vocabulary as the current articles.
Cited in PMC
Full-text articles in the PubMed Central Database that cite the current articles.

Recent activity

Clear Turn Off Turn On

General method for the synthesis of caged phosphopeptides: tools for the explora...
General method for the synthesis of caged phosphopeptides: tools for the exploration of signal transduction pathways.
Org Lett. 2002 Aug 22 ;4(17):2865-8.

PubMed
Cloning and characterization of the promoter region of the human CD83 gene.
Cloning and characterization of the promoter region of the human CD83 gene.
Immunobiology. 2002 Jul ;205(3):231-46.

PubMed
The occurrence of CMV-specific short Rnas in transgenic tobacco expressing virus...
The occurrence of CMV-specific short Rnas in transgenic tobacco expressing virus-derived double-stranded RNA is indicative of resistance to the virus.
Mol Plant Microbe Interact. 2002 Aug ;15(8):826-33.

PubMed
Screening for posttraumatic stress disorder in a general psychiatric outpatient ...
Screening for posttraumatic stress disorder in a general psychiatric outpatient setting.
J Consult Clin Psychol. 2002 Aug ;70(4):961-6.

PubMed
Multicenter trial of fluoxetine as an adjunct to behavioral smoking cessation tr...
Multicenter trial of fluoxetine as an adjunct to behavioral smoking cessation treatment.
J Consult Clin Psychol. 2002 Aug ;70(4):887-96.

PubMed

Your browsing activity is empty.

Activity recording is turned off.

Turn recording back on

PubMed

Result Filters

Display Settings:

Send to: