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Topic: Native chemical ligation

	Native chemical ligation - Wikipedia, the free encyclopedia
		Native chemical ligation is a technique for constructing a large peptide from two smaller peptides, a C-terminal thioester peptide and a N-terminal cysteine peptide.
		This process was developed by Phillip Dawson and Steven Kent at The Scripps Research Institute in 1984, about the same time that inteins were discovered, which is nature's analogous reaction.
		Peptides synthesized by native chemical ligation must be handled carefully; the thioester piece cannot be synthesized with a nucleophilic base, thus favoring BOC chemistry.
	en.wikipedia.org /wiki/Native_chemical_ligation (208 words)

	The Scripps Research Institute (Site not responding. Last check: 2007-10-15)
		We have developed a chemical approach for the production of the large polypeptide chains that comprise protein molecules, enabling us to change the structure of a protein in ways impossible by natural means.
		This ‘chemical ligation’ approach greatly facilitates the synthesis of proteins of moderate size and has opened the world of proteins to the synthetic tools of organic chemistry.
		Chemical ligation can be extended to biologically expressed proteins enabling the semisynthesis of proteins of unlimited size that contain fluorophores or cross-linking agents at defined positions.
	www.scripps.edu /research/faculty.php?tsri_id=1174 (275 words)

	TSRI - News and Publications (Site not responding. Last check: 2007-10-15)
		This chemical ligation approach greatly facilitates the synthesis of proteins of moderate size and has opened up the world of proteins to the synthetic tools of organic chemistry (Fig.
		Recently, we extended the native chemical ligation technique by increasing the number of ligation sites that can be used and by simplifying the synthesis of Cα-thioester peptides used in the ligation reaction.
		Many proteins can adopt a structure similar to the native protein even when their polypeptide chains are broken into 2 or more fragments.
	www.scripps.edu /news/sk/skaggs99/skaggs07.html (545 words)

	Department of Chemistry: Graduate Colloquium
		Chemical synthesis of peptides is limited in that only peptide chains of approximately 50 amino acids can be routinely synthesized.
		To overcome this limitation, methods to chemically ligate short peptide sequences were developed in order to synthesize large protein structures.
		Two common methods developed in the early 1990s, Native chemical ligation and expressed protein ligation, have met with some success, but also present limitations.
	www.chemistry.mcmaster.ca /colloquia/0102/colloq.20011212.html (149 words)

	Department of Chemistry and Biochemistry, UMBC (Site not responding. Last check: 2007-10-15)
		Recent advances in synthetic peptide chemistry have made it possible to chemically synthesize proteins of up to 300 amino acid residues.
		Chemical protein synthesis affords us an unprecedented opportunity to engineer proteins using novel building blocks.
		Lu, W.; Starovasnik, M.A.; Kent, S.B.H., "Total chemical synthesis of bovine pancreatic trypsin inhibitor by native chemical ligation," FEBS Lett.
	www.umbc.edu /biochem/faculty/lu/wlu.html (832 words)

	MD-PhD Research (Site not responding. Last check: 2007-10-15)
		Our research focuses on exploring the chemical basis of protein function, that is to say how the physico-chemical properties of the polypeptide chain dictate three-dimensional structure and hence biological function.
		We believe that such a chemical etiology is best attained using the combined tools of organic chemistry, structural biology and analytical biochemistry.
		We are using chemical ligation and combinatorial chemistry to study the structure-activity relationships of the SH2 and SH3 domains from the proto-oncogene non-receptor protein-tyrosine kinase c-Abl, the objectives being to understand the role that these domains play in oncogenic forms of the c-Abl protein.
	www.med.cornell.edu /mdphd/fac/muir.html (442 words)

	Expressed protein ligation: Method and applications -- David et al. 271 (4): 663 -- FEBS Journal (Site not responding. Last check: 2007-10-15)
		The bottleneck in NCL is the generation of the thioester.
		Dawson, P.E., Muir, T.W., Clark-Lewis, I. and Kent, S.B. (1994) Synthesis of proteins by native chemical ligation.
		Nilsson, B.L., Kiessling, L.L. and Raines, R.T. (2000) Staudinger ligation: a peptide from a thioester and azide.
	content.febsjournal.org /cgi/content/full/271/4/663 (7977 words)

	Protein Splicing Bibliography (Site not responding. Last check: 2007-10-15)
		Dawson, P.E. and Kent, S.B.H. (2000) Synthesis of Native Proteins by Chemical Ligation.
		Gieselman, M.D., Xie, L. and van Der Donk, W.A. (2001) Synthesis of a selenocysteine-containing peptide by native chemical ligation.
		Nilsson, B.L., Kiessling, L.L. and Raines, R.T. Staudinger Ligation: A Peptide from a Thioester and Azide.
	www.neb.com /inteins/int_bibliog.html (7893 words)

	Bertozzi Group publications
		Saxon, E.; Armstrong, J. I.; Bertozzi, C. A "Traceless" Staudinger Ligation for the Chemoselective Synthesis of Amide Bonds.
		A fluorogenic dye activated by the staudinger ligation.
		Chemical remodelling of cell surfaces in living animals.
	www.cchem.berkeley.edu /~crbgrp/publications.htm (1983 words)

	BioSpace News for
		The Innovations section of the publication is devoted to Chemical Protein Synthesis (CPS), the technique Gryphon applies to the design and manufacture of its synthetic protein therapeutics.
		SEP will be developed by Roche to treat the common conditions which cause anemia, including the treatment of cancer with chemotherapy, and hemodialysis of patients suffering from chronic renal failure.
		Gryphon Sciences and Geneva Proteomics ("GeneProt") today announced the signing of a collaboration agreement for the chemical synthesis of proteins identified by proteomic analysis of chosen biological fluids, cells and tissues in both healthy and sick individuals.
	www.biospace.com /news_company.cfm?CompanyID=2160&gls=1 (686 words)

	Biochemist e-volution: Biochemistry books
		Peptide hormones originating in various organs are described, as are neuroactive peptides, peptide antibiotics and toxins.
		Chapter 4 deals with chemical synthesis of peptides, including terminal and side-chain functional group protection, peptide bond formation and solid-phase synthesis.
		The descriptions of 'native chemical ligation' and of 'expressed protein ligation' [otherwise known as 'intein-mediated protein ligation'] show the convergence of chemical and natural protein splicing techniques.
	www.biochemist.org /reviews/page.htm?item=462 (598 words)

	Bacteriophage Ecology Group — Cyanophage References (Site not responding. Last check: 2007-10-15)
		Proteinases induced by the virus are distinguished from those of native cells by a series of physico-chemical characteristics and possess higher catalytic activity.
		The differences between chemical structures of the A:U and I:C or the A:T and I:m5C base-pairs seem to be unimportant for the thermostability of the DNA.
		Analysis of native and cloned A-4L DNA suggests that counter-selection has occurred against all sequences which would be methylated by the host at either adenosine or cytosine nucleotides.
	www.mansfield.ohio-state.edu /~sabedon/bib_cp.htm (17368 words)

	Wuyuan Lu - Biography - Institute of Human Virology (Site not responding. Last check: 2007-10-15)
		Lu's major scientific expertise and research achievements lie in using both genetic and chemical protein engineering approaches to elucidate the molecular basis of protein recognition.
		Lu, W., Starovasnik, M.A. and Kent, S.B.H. Total chemical* synthesis of bovine pancreatic trypsin inhibitor by native chemical ligation.
		Deciphering the role of the electrostatic interactions involving Gly70 in eglin c by total chemical protein synthesis.
	www.ihv.org /bios/lu.html (739 words)

	UVM Biochemistry: Dr. Robert Hondal, Ph.D. (Site not responding. Last check: 2007-10-15)
		He then spent one year in the laboratory of Raymond Burk at Vanderbilt University studying the chemistry of selenomethionine and the structure of selenoprotein P. He continued his postdoctoral study under the direction of Ronald Raines at the University of Wisconsin-Madison as a NIH Postdoctoral Fellow.
		His work there focused on state of the art protein engineering techniques, including native chemical ligation and expressed protein ligation.
		Selenocysteine in native chemical ligation and expressed protein ligation.
	biochem.uvm.edu /individualfaculty.php?id=76 (338 words)

	Supramolecular Architectures (Site not responding. Last check: 2007-10-15)
		Native Chemical Ligation is a commonly used synthetic method for the coupling of two peptide fragments.
		If these fragments are combined under mild conditions (pH 7.5, buffered media, no protective groups), a chemical reaction takes place, followed by a spontaneous rearrangement yielding a native peptide bond (see former quarterly reports).
		The aim of research is to combine dendrimers and peptides via Native Chemical Ligation and study their application in biologics and medicine.
	www.chem.tue.nl /smo/groups/bmt/supramol_arch.htm (464 words)

	A Tribute to Hinduism - Hindu Culture2 (Site not responding. Last check: 2007-10-15)
		This might be expected, because their patient attention and natural shrewdness would render them excellent observers, whilst the extent and fertility of their native country would furnish them with many valuable drugs and medicaments.
		He was the first to graft upon a torn ear portions of skin taken from another part of the body; and from him and his Indian successors rhinoplasty- the surgical reconstruction of the nose-descended into modern medicine.
		The 32nd chapter of the manuscript is devoted to signs of earthquakes and correlates earthquakes with cosmic and planetary influences, underground water and undersea activities, unusual cloud formations, and the abnormal behavior of animals.
	www.atributetohinduism.com /Hindu_Culture2.htm (10936 words)

	EnGeM: Work Description (Site not responding. Last check: 2007-10-15)
		Since engineering of restriction endonucleases and DNA methyltransferases based on so-called rational approaches turned out to be extremely difficult for the development of DNA modifying enzymes with programmable specificities, chemical methods which allow specific coupling of enzymes with ODNs or PNAs capable of forming a triple helix on DNA will be used.
		Mutants of these enzymes, which are suitable for coupling with ODN and PNA and which have been optimised for DNA-binding will be produced and purified in large quantities.
		Three different coupling methods to ODN or PNA affinity tags will be explored: 1) classical coupling using heterobifunctional crosslinking reagents, 2) native chemical peptide ligation (NCPL), and 3) intein-mediated protein ligation (IPL).
	www.stepc.gr /ENGEM/wdescription.htm (309 words)

	Selected Publications
		Solid-Phase Synthesis and Chemical Ligation of Transmembrane Segments of Rhodopsin
		First is the determination, by chemical modification and biological testing, of the relative importance of different funtional groups in the drug to receptor recognition.
		The only difference between the chemical structures of the linear analogues compared to the cyclic ones is that one covalent bond has been eliminated and a sulfur atom is replaced by a methyl group.
	www.cmd.wustl.edu /Publications.htm (3973 words)

	Peptide synthesis - Wikipedia, the free encyclopedia
		Fragment condensation is also undesirable since the coupled fragment must be in gross excess, which may be a limitation depending on the length of the fragment.
		One way around this limitation is native chemical ligation.
		This page was last modified 21:47, 21 July 2005.
	en.wikipedia.org /wiki/Peptide_synthesis (534 words)

	(WO 03/106615) POST-CLEAVAGE SULFUR DEPROTECTION FOR CONVERGENT PROTEIN SYNTHESIS BY CHEMICAL LIGATION (Site not responding. Last check: 2007-10-15)
		(57) The present invention provides a method and compositions for synthesizing an oligopeptide or polypeptide by convergent assembly of a plurality of pairs of oligopeptides in chemical ligation reactions.
		This allows a single precursor to participate in a succession of chemical ligation reactions, thereby making the convergent synthesis approach possible.
		The present invention is useful in methods for chemical synthesis of oligopeptides, polypeptides and proteins, and improves the efficiency of native chemical ligation reactions, particularly where four or more peptide fragments are used to assemble an oligopeptide, polypeptide or protein product.
	wipo.int /ipdl/IPDL-CIMAGES/view/pct/getbykey5?KEY=03/106615.031224&... (229 words)

	(WO 01/87920) LIGATION METHOD AND REAGENTS TO FORM AN AMIDE BOND (Site not responding. Last check: 2007-10-15)
		LIGATION METHOD AND REAGENTS TO FORM AN AMIDE BOND
		The invention provides phosphinothiol reagents which convert activated carboxylic acid derivatives to phosphinothioesters which then react with azides to form an amide bond.
		The methods and reagents of the invention can be used for stepwise synthesis of peptides on solid supports or for the ligation to two or more amino acids, two or more peptide or two or more protein fragments.
	wipo.int /ipdl/IPDL-CIMAGES/view/pct/getbykey5?KEY=01/87920.011122&... (233 words)

	Intein - free-definition (Site not responding. Last check: 2007-10-15)
		Since then, inteins have been found in all three domains of life (eukaryotes, bacteria, and archaea).
		The mechanism for the splicing effect is nature's analogy to the technique for chemically generating large proteins called native chemical ligation, which was developed at the same time as inteins were discovered.
		Inteins are very efficient at protein splicing and they have accordingly found an important role in biotechnology.
	www.free-definition.com /Intein.html (471 words)

	AECOM CSB Publications
		Solomon, A., Rosenblum, G.,Gonzales, P.E., Leonard, J.D., Mobashery, S.,Milla, M.E., Sagi, I. Pronounced Diversity in Electronic and Chemical Properties Between the Catalytic Zinc Sites of TACE and MMP’s Despite their High Structural Similarity.
		Yu, P., McKinnon, J.J., Christensen, C.R., Christensen, D.A. Use of Synchrotron-Base FTIR Microspectroscopy to Reveal Chemical Features of Feather Protein Secondary Structure and Its Relation to Protein Value.
		Miller, L.M., Tibrewala, J., Carlson, C. Examination of Bone Chemical Composition in Osteoporosis Using Luorescence-Assisted Synchrotron Infrared Microspectroscopy.
	www.aecom.yu.edu /home/csb/publications.htm (4765 words)

	Protein & Peptide Letters, Volume 11, No. 2, 2004 (Site not responding. Last check: 2007-10-15)
		These reactions suggest an approach for the incorporation of unnatural amino acids into proteins by successive native chemical ligation and Staudinger ligation.
		coupling constants, temperature coefficients of NH chemical shifts and the pattern of intra and inter-residue nOe's.
		The association domain of the enzyme has been crystallized in its native multimeric form after expression in E. coli [Hoelz, A., Nairn, A. and Kuriyan, J. (2003) Molecular Cell 11, 1241].
	www.bentham.org /ppl/ppl11-2.htm (1593 words)

	The orientation of the AP-1 heterodimer on DNA strongly affects transcriptional potency -- Chytil et al. 95 (24): 14076 ...
		Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138
		EDTA by using native chemical ligation as described previously
		Using a native chemical ligation/affinity cleavage procedure to detect directly the orientation of the AP-1 bZip on DNA, here
	www.pnas.org /cgi/content/full/95/24/14076 (3970 words)

	Cancer Research Laboratory 2003-2004
		Due to the large increase in user base (over 80 users from over 40 different labs, including 7 different campus departments, LBNL, and 1 industry), we added an off-line computer workstation in October 2003 for analyzing data post acquisition.
		This workstation allows users to view their data in the native Zeiss format, as well as backup data, and analyze data.
		Recently, a license for Bitplane’s Imaris Imaging Suite software was added to allow users to view and quantitate their 3D and 4D datasets.
	www.biol.berkeley.edu /crl/crl_annual_report.html (4226 words)

	Chemistry at the University of Edinburgh - Dr. Derek MacMillan (Site not responding. Last check: 2007-10-15)
		This involves using selective protein-carbohydrate coupling reactions on solid-phase followed by cleavage from the resin to afford glycopeptide
		-thioesters which contain the suitable reactive functional group (thioesters) for sticking protein fragments together in a reaction known as native chemical ligation.
		Typical projects include synthesis of oligosaccharides and glycopeptides, screening of synthetic products against available enzymes for structural elaboration, molecular biology and expression of protein fragments suitable for native chemical ligation, application of protein fragment coupling reactions to solid-phase assembly, and exploration of new methods for the synthesis of glycopeptide
	www.chem.ed.ac.uk /staff/macmillan.html (500 words)

	Peptide Day 2005 (Site not responding. Last check: 2007-10-15)
		Remco Merkx (UU): Highly efficient coupling of beta-substituted aminoethane sulfonyl azides with thio acids, toward a new chemical ligation reaction.
		Rob Hoen (RUG): Rhodium-catalyzed asymmetric hydrogenation: An efficient route to b2 amino acids.
		Hinke Malda (TUE): Multivalent Peptide Dendrimers in Biomedical Applications; Native Chemical Ligation as a tool.
	www.orgchem.science.ru.nl /news_events/peptide_day/peptide_day.htm (249 words)

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