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Topic: Lanthionine

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	Lanthionine bridged peptides - Patent 6028168 (Site not responding. Last check: 2007-10-08)
		This thioether bond is also designated as a lanthionine bridge and corresponds with the cystine bridge with the exception that the disulfide bridge is replaced by a monosulfide linkage.
		Thus the synthesis of.beta.-methyl lanthionines and.beta.,.beta.-dimethyl lanthionine results in modifications, which are expected to lead to substantial differences in bioactivity profiles for closely related target molecules.
		It is possible to incorporate the lanthionine as the replacement of the cysteine-cysteine disulfide bridge in the N-terminal loop.
	www.freepatentsonline.com:9003 /6028168.html (5717 words)

	Patent 6,521,596
		The purified peptide is pH- and temperature-stable and its amino acid composition indicates the presence of lanthionine and.beta.-methyllanthionine.
		In the place of expected serines and threonines were the lanthionine and.beta.-methyllanthiones; other residues were apparently dehydrated it thus became clear that the mature nisin molecule was the result of posttranslational modifications, thereby prompting a search for these otherwise unknown processing enzymes began.
		Both lanthionine and methyllanthionine are expected to be suitable for cleavage from protein with the Edman procedure.
	www.pharmcast.com /Patents/Yr2003/Feb2003/021803/6521596_Antibiotic021803.htm (4704 words)

	Lanthionine antibiotic compositions and method - US Patent 6521596 (Site not responding. Last check: 2007-10-08)
		The purified peptide is pH- and temperature-stable and its amino acid composition indicates the presence of lanthionine and β-methyllanthionine.
		In the place of expected serines and threonines were the lanthionine and β-methyllanthiones; other residues were apparently dehydrated it thus became clear that the mature nisin molecule was the result of posttranslational modifications, thereby prompting a search for these otherwise unknown processing enzymes began.
		One of the peaks was subsequently identified as lanthionine by comparison with the elution position of authentic lanthionine derivatized with the standard reagent.
	www.patentstorm.us /patents/6521596.html (18798 words)

	Inhibition of lanthionine formation during alkaline treatment of keratinous fibers - Patent 4212800
		Both lysinoalanine and lanthionine formation are inhibited in the alkaline treatment of keratinous fibers containing lysine by acylating the.epsilon.-amino group of lysine with an acyl moiety containing from one to eight carbon atoms.
		The sequence of reactions culminating in the formation of lanthionine may be illustrated as follows: ##STR3## Cysteine in the presence of alkali combines with a dehydroalanine unit to give lanthionine.
		Lanthionine is formed by bonding between the vinyl group of the dehydroalanine unit and the sulfhydryl group of cysteine; acylation of the above-mentioned nature should not prevent such bonding.
	www.freepatentsonline.com /4212800.html (2761 words)

	Patent 6,794,181
		The thioether lanthionine is formed when the double bond in Dha is attacked by the thiol (--SH) group of a neighboring cysteine residue.
		The presence of these lanthionine rings is thought to be essential for a number of important lantibiotic properties including, for example, maintenance of peptide rigidity and resistance to thermal inactivation.
		Thus, white the Exemplification section focuses primarily on the lantibiotic nisin, the principles established herein would be expected to apply to all lantibiotics due to the presence of their defining structural characteristics.
	www.pharmcast.com /Patents100/Yr2004/Sept2004/092104/6794181_Lantiobiotics092104.htm (2557 words)

	AAA of lanthionine (Site not responding. Last check: 2007-10-08)
		The commercially available lanthionine gave two peaks under standard conditions: a major one eluting approx.
		Unfortunately, we could not detect it in hydrolyzed samples although the peptide contained at least one lanthionine.
		When performing standard HCl hydrolysis followed by aaa with postcolumn ninhydrin detection we see the lanthione peak at about 50% the amount we would expect.
	www.abrf.org /archives/email/sel_com/aaa/lanthio1.html (244 words)

	Biosynthesis of Lantibiotic Nisin -- Siegers et al. 271 (21): 12294 -- Journal of Biological Chemistry
		Nisin is a ribosomally synthesized peptide antibiotic containing the unusual amino acids lanthionine, dehydrobutyrine, and dehydroalanine(1, 2).
		We propose the existence of a lanthionine synthetase complex of at least 350 kDa consisting of NisB, at least two molecules of NisC, and a NisT dimer (Fig.
		However, the genetic and biochemical data gave convincing evidence that lantibiotic prepeptides are matured at a multimeric lanthionine synthetase complex that catalyzes the dehydration of amino acid residues and the subsequent thioether formation between the dehydrated residues and neighboring cysteine residues within the lantibiotic prepeptides.
	www.jbc.org /cgi/content/full/271/21/12294 (6170 words)

	Replacement of diaminopimelic acid by cystathionine or lanthionine in the peptidoglycan of Escherichia coli -- ...
		Replacement of diaminopimelic acid by cystathionine or lanthionine in the peptidoglycan of Escherichia coli -- Mengin-Lecreulx et al.
		suppressed by growth with exogenous cystathionine or lanthionine.
		An Unusual Mutation Results in the Replacement of Diaminopimelate with Lanthionine in the Peptidoglycan of a Mutant Strain of Mycobacterium smegmatis.
	jb.asm.org /cgi/content/abstract/176/14/4321 (552 words)

	Characterization of rat LANCL1, a novel member of the lanthionine synthetase C-like protein family, highly expressed in ... (Site not responding. Last check: 2007-10-08)
		Characterization of rat LANCL1, a novel member of the lanthionine synthetase C-like protein family, highly expressed in testis and brain.LanC is involved in the synthesis of antimicrobial peptides.
		We isolated and characterized the cDNA coding for rat LANCL1, a new member of the eukaryotic LanC-like protein family which is related to the bacterial lanthionine synthetase components C (LanC).
		In situ hybridization analyses of various rat tissues revealed a strong signal in the germinal cells of the seminiferous tubules in testis, in the neurons of the cerebellum, in liver hepatocytes, and in cardiac myocytes.
	www.pdg.cnb.uam.es /UniPub/iHOP/gp/8972770.html (238 words)

	BioMaDe
		Lanthionines are special thioether containing amino which are posttranslationally introduced into peptides via dehydration of serines and threonines and subsequent coupling of these dehydrated residues to cysteine residues.
		The (methyl)lanthionines in nisin are synthesised by a membrane associated enzyme cluster composed of a dehydrating enzyme, a ring-forming enzyme, and a transporter.
		BiOMaDe researchers are focusing on gaining full control of the enzyme complex in order to develop an entirely biosynthetic means to introduce lanthionine rings into peptides and proteins, thereby generating new peptide antibiotics as well as to stabilizing therapeutic peptides and proteins against proteolytic degradation.
	www.biomade.nl /LanthionineBiosynthesis.htm (199 words)

	Lanthionine antibiotic compositions and methods - Patent 5650320
		It is now clear that mutacin II group belongs to the lanthionine family of antibiotics.
		Another cloning approach contemplated to be particularly suitable is the use of a probe or primer directed to a gene known to be generally associated with, e.g., within the same operon as, the structural gene that one desires to clone.
		For example, in the case of mutacin, one may wish to use a primer directed to the conserved ABC transporter genes that are known to be associated with all lanthionine antibiotic genes.
	www.freepatentsonline.com /5650320.html (18166 words)

	[No title] (Site not responding. Last check: 2007-10-08)
		Lantibiotics are polycyclic peptides with several intrachain sulfide bridges, consisting of the thioether amino acids lanthionine and B-methyllanthionine (Jung, 1991).
		likely not choose to change the lanthionine or b-methyllanthionine residues which are particularly characteristic of this type of antibiotic.
		One of the peaks was subsequently identified a s lanthionine by comparison with the elution position of authentic lanthionine derivatized with the standard reagent.
	www.wipo.int /cgi-pct/guest/getbykey5?KEY=98/17685.980813&ELEMENT_SET=DECL (10610 words)

	Amit Abstract & Manuscript
		Using this reaction, lanthionine, cystathionine, and penthionine (a novel thioether-bridged amino acid) containing cyclic peptides have been synthesized from their cysteine, homocysteine and penicillamine precursors, respectively.
		Interestingly, later it was realized that several sulfur-rich proteins undergo facile desulfurization but there are no reported examples of facile thioether formation from the action of alkali on small organic disulfides such as free cystine or its analogs (3).
		The stereochemical analysis (as assessed by TOCSY, HSQC and amino acid analysis experiments) revealed that in the case of lanthionine formation, the reaction shows lack of regioselectivity in proton abstraction as well as the lack of stereoselectivity in Michael-addition.
	www.imd3.org /amitmanuscriptabstract.html (825 words)

	Lanthionine - TheBestLinks.com - Amino acid, Peptide, Cysteine, Alanine, ... (Site not responding. Last check: 2007-10-08)
		Lanthionine - TheBestLinks.com - Amino acid, Peptide, Cysteine, Alanine,...
		Lanthionine, Amino acid, Peptide, Cysteine, Alanine, Unsaturated, Proteinogenic...
		You can add this article to your own "watchlist" and receive e-mail notification about all changes in this page.
	www.thebestlinks.com /Lanthionine.html (115 words)

	Applied NanoSystems
		The lanthionine ring introduces additional 3D structure in the protein and reduces its susceptibility to proteolytic degradation.
		BiOMaDe researchers have gained control of this system and developed a generic protein/peptide technology for biosynthetically incorporating lanthionine rings into existing proteins or peptides and exporting them into the growth medium to be easily recovered by a proprietary single step isolation procedure.
		Currently, the generality of this technology is being demonstrated by introducing the lanthionine ring into peptides and proteins of different sizes and carrying out proof-of-principle studies on two commercially important therapeutic peptides.
	ans-bv.nl /therapeutic.htm (305 words)

	[No title] (Site not responding. Last check: 2007-10-08)
		Not to be limited by theory, there are two reaction sequences that are predominantly used to explain the disruption of the disulfide bonds in hair by hydroxide ions, both of which result in lanthionine formation.
		One sequence is a bimolecular nucleophilic substitution mechanism where the hydroxide ion directly attacks the disulfide linkage, resulting in the formation of lanthionine and HOS.
		Thus, the term lanthionizing is used when one skilled in the art refers to the relaxing or straightening of keratin fibers by hydroxide ions.
	www.wipo.int /cgi-pct/guest/getbykey5?KEY=01/64171.010907&ELEMENT_SET=DECL (6441 words)

	Pfam 18.0 : LANC_like (Site not responding. Last check: 2007-10-08)
		This family contains the lanthionine synthetase C-like proteins 1 and 2 which are related to the bacterial lanthionine synthetase components C (LanC).
		Both proteins are produced in large quantities in the brain and testes and may have role in the immune surveillance of these organs [1].
		Both proteins are produced in large quantities in the brain and testes and may have role in the immune surveillance of these organs MEDLINE:11376939.
	pfam.wustl.edu /cgi-bin/getdesc?acc=PF05147 (179 words)

	Pfam 18.0 : L_biotic_typeA (Site not responding. Last check: 2007-10-08)
		Lantibiotics are antibiotic peptides distinguished by the presence of the rare thioether amino acids lanthionine and/or methyllanthionine.
		They are produced by Gram-positive bacteria as gene-encoded precursor peptides and undergo post-translational modification to generate the mature peptide.
		Based on their structural and functional features lantibiotics are currently divided into two major groups: the flexible amphiphilic type-A and the rather rigid and globular type-B. Type-A lantibiotics act primarily by pore formation in the bacterial membrane by a mechanism involving the interaction with specific docking molecules such as the membrane precursor lipid II [1].
	pfam.wustl.edu /cgi-bin/getdesc?name=L_biotic_typeA (147 words)

	Post-translational modification of nisin: The involvement of NisB in the dehydration process -- Karakas Sen et al. 261 ... (Site not responding. Last check: 2007-10-08)
		Abbreviations: Dha, dehydroalanine; Dhb, dehydrobutyrine; Lan, lanthionine; MeLan,
		The amino acid substitutions introduced in the nisin variants used in this study are indicated together with the unmodified Ser33 residue, that occurs as a result of partial processing.
		Siegers, K., Heinzmann, S. and Entian, K.D. (1996) Biosynthesis of lantibiotic nisin – Posttranslational modification of its prepeptide occurs at a multimeric membrane-associated lanthionine synthetase complex.
	content.febsjournal.org /cgi/content/full/261/2/524 (5317 words)

	NMR group Nijmegen University: Structure Gallery (Site not responding. Last check: 2007-10-08)
		The lantibiotic nisin is a cationic, polycyclic bacteriocin of 34 residues, including several unusual dehydro residues and thioether-bridged lanthionines.
		The structure consists of two structured domains: an N-terminal domain (residues 3-19) containing three lanthionine rings, A, B and C; and a C-terminal domain (residues 22-28) containing two intertwined lanthionine rings numbered D and E. These domains are flanked by regions showing structural variability.
		Preceding the intertwined rings D (residues 23-26) and E (25-28) another type-II beta-turn is found formed by the residues 21-24, so that the C-terminal domain consists of three consecutive beta-turns.
	www.nmr.kun.nl /bfc/Structures/NISINE/NISINE.html (300 words)

	NisB is required for the dehydration and NisC for the lanthionine formation in the post-translational modification of ...
		reaction but seems to be involved in correct lanthionine formation.
		It is known that all lanthionines are needed for nisin activity
		Siegers, K., Heinzman, S. and Entian, K.-D. Biosynthesis of lantibiotic nisin – posttranslational modification of its prepeptide occurs at a multimeric membrane-associated lanthionine synthetase complex.
	mic.sgmjournals.org /cgi/content/full/148/11/3561 (4069 words)

	List of Publications 2003
		These fragments specifically resulted from the cleavage of both a backbone amine bond and the thioether bond in a lanthionine bridge.
		This fragmentation pattern indicates that lanthionine bridges play a key role in the selectivity of the ECD process.
		Our results suggest that ECD can be used as a tool to identify the C-terminal attachment site of lanthionine bridges in newly discovered lantibiotics.
	www.amolf.nl /publications/list_of_publications/list_of_publications_2003.html (5680 words)

	IFR Science Brief - Latest news on biological control strategies (Site not responding. Last check: 2007-10-08)
		Much of this work is focused on nisin, produced by certain strains of the LAB species Lactococcus lactis and used widely by the food industry.
		Nisin and other lantibiotics are synthesised as the product of a gene, but the resultant peptide is subject to post-translational modification to generate the mature molecule, complete with its lanthionine rings.
		The biosynthetic process is complex and involves a cluster of genes with a variety of functions.
	www.ifrn.bbsrc.ac.uk /science/sciencebriefs/lactic.html (447 words)

	An Unusual Mutation Results in the Replacement of Diaminopimelate with Lanthionine in the Peptidoglycan of a Mutant ...
		Identification of lanthionine in the peptidoglycan of strain PM440 grown in the absence of DAP.
		Structural diagrams of DAP and lanthionine are inset into panels A and B, respectively.
		be a precursor for lanthionine (24), we decided to examine the
	jb.asm.org /cgi/content/full/187/5/1612 (4703 words)

	Systemic and Spinal Analgesic Activity of a {delta}-Opioid-Selective Lanthionine Enkephalin Analog -- Svensson et al. ...
		denote the lanthionine amino acid ends linked by a monosulfide bridge to form the lanthionine structure.
		Wang SHH (1996) Studies of lanthionine peptides and the use of urethane-protected N-carboxyanhydrides in solid phase peptide synthesis, in Chemistry and Biochemistry, pp 77–106, University of California Press, San Diego, CA.
		Wang SHH, Bahmanyar S, Taulane JP, and Goodman M (1996) Enzymic stability of disulfide-bridged peptides and their lanthionine analogs, in Peptides: Chemistry, Structure and Biology (Proceedings of the 14th American Peptide Symposium) (Kumaya PTP and Hodges RS eds) pp 715–716, Mayflower Scientific, Kingswinford, UK.
	jpet.aspetjournals.org /cgi/content/full/304/2/827 (2833 words)

	Solution structure of plantaricin C, a novel lantibiotic -- Turner et al. 264 (3): 833 -- FEBS Journal (Site not responding. Last check: 2007-10-08)
		C to open the lanthionine bridges, prior to sequencing, was
		bridge in lanthionine was constructed by superimposing the C
		Lanthionines are shown as linked open circles and the position of the methyl group in methyl lanthionines is marked `m'.
	content.febsjournal.org /cgi/content/full/264/3/833 (4160 words)

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