923-16-0 | D-Alanyl-D-alanine

Packsize	Purity	Availability	Price	Discounted Price
100mg	95%	in stock	$45.00	$32.00
250mg	95%	in stock	$56.00	$40.00
1g	95%	in stock	$126.00	$89.00

Description

• Catalog Number: AI61730
• Chemical Name: D-Alanyl-D-alanine
• CAS Number: 923-16-0
• Molecular Formula: C6H12N2O3
• Molecular Weight: 160.1711
• MDL Number: MFCD00066038
• SMILES: C[C@H](C(=O)O)NC(=O)[C@H](N)C

Computed Properties

• Complexity: 169
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 2
• Heavy Atom Count: 11
• Hydrogen Bond Acceptor Count: 4
• Hydrogen Bond Donor Count: 3
• Rotatable Bond Count: 3
• XLogP3: -3.3

Literature

• Purification, biochemical, and structural characterization of a novel fibrinolytic enzyme from Mucor subtilissimus UCP 1262.

  Bioprocess and biosystems engineering 20170801

• Atomic multipoles: electrostatic potential fit, local reference axis systems, and conformational dependence.

  Journal of computational chemistry 20120730

• Intestinal permeability of cyclic peptides: common key backbone motifs identified.

  Journal of the American Chemical Society 20120725

• An algorithm to find minimum free-energy paths using umbrella integration.

  The Journal of chemical physics 20120721

• Oritavancin: mechanism of action.

  Clinical infectious diseases : an official publication of the Infectious Diseases Society of America 20120401

• Structure and function of the transketolase from Mycobacterium tuberculosis and comparison with the human enzyme.

  Open biology 20120101

• Force-momentum-based self-guided Langevin dynamics: a rapid sampling method that approaches the canonical ensemble.

  The Journal of chemical physics 20111128

• A porous silicon optical microcavity for sensitive bacteria detection.

  Nanotechnology 20111021

• Gay-Berne and electrostatic multipole based coarse-grain potential in implicit solvent.

  The Journal of chemical physics 20111021

• Multiple state transition interface sampling of alanine dipeptide in explicit solvent.

  The Journal of chemical physics 20111014

• Reactivity of alanylalanine diastereoisomers in neutral and acid aqueous solutions: a versatile stereoselectivity.

  Origins of life and evolution of the biosphere : the journal of the International Society for the Study of the Origin of Life 20111001

• Clonal structure of Streptococcus sanguinis strains isolated from endocarditis cases and the oral cavity.

  Molecular oral microbiology 20111001

• A redesigned vancomycin engineered for dual D-Ala-D-ala And D-Ala-D-Lac binding exhibits potent antimicrobial activity against vancomycin-resistant bacteria.

  Journal of the American Chemical Society 20110907

• Perturbation analyses of intermolecular interactions.

  Physical review. E, Statistical, nonlinear, and soft matter physics 20110801

• Probing peptide-inorganic surface interaction at the single molecule level using force spectroscopy.

  Chemphyschem : a European journal of chemical physics and physical chemistry 20110509

• Toward canonical ensemble distribution from self-guided Langevin dynamics simulation.

  The Journal of chemical physics 20110407

• Integrating diffusion maps with umbrella sampling: application to alanine dipeptide.

  The Journal of chemical physics 20110407

• Dissociative electron attachment to glycyl-glycine, glycyl-alanine and alanyl-alanine.

  Physical chemistry chemical physics : PCCP 20110314

• Bond dissociation of the dipeptide dialanine and its derivative alanine anhydride induced by low energy electrons.

  The Journal of chemical physics 20110207

• Structure-based modification of D-alanine-D-alanine ligase from Thermotoga maritima ATCC 43589 for depsipeptide synthesis.

  Bioscience, biotechnology, and biochemistry 20110101

• Acquisition and assimilation of nitrogen as peptide-bound and D-enantiomers of amino acids by wheat.

  PloS one 20110101

• Genome-wide dynamics of a bacterial response to antibiotics that target the cell envelope.

  BMC genomics 20110101

• Exploring internal features of 16S rRNA gene for identification of clinically relevant species of the genus Streptococcus.

  Annals of clinical microbiology and antimicrobials 20110101

• A rapid in situ procedure for determination of bacterial susceptibility or resistance to antibiotics that inhibit peptidoglycan biosynthesis.

  BMC microbiology 20110101

• Identification and Characterization of Cell Wall Proteins of a Toxic Dinoflagellate Alexandrium catenella Using 2-D DIGE and MALDI TOF-TOF Mass Spectrometry.

  Evidence-based complementary and alternative medicine : eCAM 20110101

• Unique residues involved in activation of the multitasking protease/chaperone HtrA from Chlamydia trachomatis.

  PloS one 20110101

• Infrared spectroscopy of the alanine dipeptide analog in liquid water with DFT-MD. Direct evidence for P(II)/beta conformations.

  Physical chemistry chemical physics : PCCP 20100921

• Direct fluorescence polarization assay for the detection of glycopeptide antibiotics.

  Analytical chemistry 20100815

• Crystal structure of a complex between the Actinomadura R39 DD-peptidase and a peptidoglycan-mimetic boronate inhibitor: interpretation of a transition state analogue in terms of catalytic mechanism.

  Biochemistry 20100803

• Synthesis of a D-Ala-D-Ala peptide isostere via olefin cross-metathesis and evaluation of vancomycin binding.

  Bioorganic & medicinal chemistry letters 20100801

• Steady-state simulations using weighted ensemble path sampling.

  The Journal of chemical physics 20100707

• Role of Arg301 in substrate orientation and catalysis in subsite 2 of D-alanine:D-alanine (D-lactate) ligase from Leuconostoc mesenteroides: a molecular docking study.

  Journal of molecular graphics & modelling 20100601

• Multicanonical ab inito QM/MM molecular dynamics simulation of a peptide in an aqueous environment.

  Journal of computational chemistry 20100430

• Replica-exchange method in van der Waals radius space: overcoming steric restrictions for biomolecules.

  The Journal of chemical physics 20100407

• Crystallization and preliminary X-ray analysis of a D-alanyl-D-alanine ligase (EcDdlB) from Escherichia coli.

  Acta crystallographica. Section F, Structural biology and crystallization communications 20100401

• Telavancin's interactions with the bacterial cell membrane.

  Future microbiology 20100301

• Application of nonlinear dimensionality reduction to characterize the conformational landscape of small peptides.

  Proteins 20100201

• Fluoroolefins as peptide mimetics. 2. A computational study of the conformational ramifications of peptide bond replacement.

  The journal of physical chemistry. A 20100121

• A liquid chromatography-tandem mass spectrometry assay for Marfey's derivatives of L-Ala, D-Ala, and D-Ala-D-Ala: application to the in vivo confirmation of alanine racemase as the target of cycloserine in Escherichia coli.

  Analytical biochemistry 20100101

• Global gene expression under nitrogen starvation in Xylella fastidiosa: contribution of the σ54 regulon.

  BMC microbiology 20100101

• Proteomic characterization of vanA-containing Enterococcus recovered from Seagulls at the Berlengas Natural Reserve, W Portugal.

  Proteome science 20100101

• Deciphering the intracellular metabolism of Listeria monocytogenes by mutant screening and modelling.

  BMC genomics 20100101

• Introducing sampling entropy in repository based adaptive umbrella sampling.

  The Journal of chemical physics 20091207

• A selective integrated tempering method.

  The Journal of chemical physics 20091207

• Molecular mechanics force field-based map for peptide amide-I mode in solution and its application to alanine di- and tripeptides.

  Physical chemistry chemical physics : PCCP 20091028

• Exploration of effective potential landscapes using coarse reverse integration.

  The Journal of chemical physics 20091007

• Direct calculations of vibrational absorption and circular dichroism spectra of alanine dipeptide analog in water: quantum mechanical/molecular mechanical molecular dynamics simulations.

  The Journal of chemical physics 20091007

• On-capillary derivatization using a hybrid artificial neural network-genetic algorithm approach.

  The Analyst 20091001

• Numerical examination of the extended phase-space volume-preserving integrator by the Nosé-Hoover molecular dynamics equations.

  Journal of computational chemistry 20090901

• Reconstructing the equilibrium Boltzmann distribution from well-tempered metadynamics.

  Journal of computational chemistry 20090801

• Abstracts of the 2008 ISSOL Meeting. August 24-29, 2008. Florence, Italy.

  Origins of life and evolution of the biosphere : the journal of the International Society for the Study of the Origin of Life 20090801

• Absolute free energies estimated by combining precalculated molecular fragment libraries.

  Journal of computational chemistry 20090801

• L-alanyl-L-alanine conformational changes induced by pH as monitored by the Raman optical activity spectra.

  The journal of physical chemistry. A 20090709

• Adaptive anisotropic kernels for nonparametric estimation of absolute configurational entropies in high-dimensional configuration spaces.

  Physical review. E, Statistical, nonlinear, and soft matter physics 20090701

• Use of magnetic beads to study the interaction of ristocetin with peptides and bacteria.

  Bioanalysis 20090701

• Exploring the free energy landscape: from dynamics to networks and back.

  PLoS computational biology 20090601

• In vivo transcriptional profiling of Listeria monocytogenes and mutagenesis identify new virulence factors involved in infection.

  PLoS pathogens 20090501

• Theoretical study of the effective Chemical Shielding Anisotropy (CSA) in peptide backbone, rating the impact of CSAs on the cross-correlated relaxations in L-alanyl-L-alanine.

  The journal of physical chemistry. B 20090416

• Comparison between integrated and parallel tempering methods in enhanced sampling simulations.

  The Journal of chemical physics 20090328

• Carbon-deuterium vibrational probes of peptide conformation: alanine dipeptide and glycine dipeptide.

  The Journal of chemical physics 20090328

• Design and synthesis of new hydroxyethylamines as inhibitors of D-alanyl-D-lactate ligase (VanA) and D-alanyl-D-alanine ligase (DdlB).

  Bioorganic & medicinal chemistry letters 20090301

• Telavancin: a new lipoglycopeptide for gram-positive infections.

  Drugs of today (Barcelona, Spain : 1998) 20090301

• Vancomycin resistance: modeling backbone variants with D-Ala-D-Ala and D-Ala-D-Lac peptides.

  Bioorganic & medicinal chemistry letters 20090215

• Structure of PBP-A from Thermosynechococcus elongatus, a penicillin-binding protein closely related to class A beta-lactamases.

  Journal of molecular biology 20090213

• Poisoning pyridoxal 5-phosphate-dependent enzymes: a new strategy to target the malaria parasite Plasmodium falciparum.

  PloS one 20090101

• In silico prioritisation of candidate genes for prokaryotic gene function discovery: an application of phylogenetic profiles.

  BMC bioinformatics 20090101

• DD-ligases as a potential target for antibiotics: past, present and future.

  Current medicinal chemistry 20090101

• Genome-scale gene/reaction essentiality and synthetic lethality analysis.

  Molecular systems biology 20090101

• Bench-to-bedside review: Understanding the impact of resistance and virulence factors on methicillin-resistant Staphylococcus aureus infections in the intensive care unit.

  Critical care (London, England) 20090101

• Expression, crystallization and preliminary X-ray crystallographic analysis of Xoo0352, D-alanine-D-alanine ligase A, from Xanthomonas oryzae pv. oryzae.

  Acta crystallographica. Section F, Structural biology and crystallization communications 20081201

• Synthesis and structural study of cyclic 5-aminovaleric acid-linked beta-Ala-beta-Ala dipeptides.

  Bioorganic & medicinal chemistry letters 20081115

• Characterization of structural variations in the peptidoglycan of vancomycin-susceptible Enterococcus faecium: understanding glycopeptide-antibiotic binding sites using mass spectrometry.

  Journal of the American Society for Mass Spectrometry 20081001

• A versatile AMBER-Gaussian QM/MM interface through PUPIL.

  Journal of computational chemistry 20080730

• Ethanol inhibits functional activity of the human intestinal dipeptide transporter hPepT1 expressed in Xenopus oocytes.

  Alcoholism, clinical and experimental research 20080501

• Vancomycin derivative with damaged D-Ala-D-Ala binding cleft binds to cross-linked peptidoglycan in the cell wall of Staphylococcus aureus.

  Biochemistry 20080325

• Characterization of tRNA-dependent peptide bond formation by MurM in the synthesis of Streptococcus pneumoniae peptidoglycan.

  The Journal of biological chemistry 20080307

• Determination of conformational preferences of dipeptides using vibrational spectroscopy.

  The journal of physical chemistry. B 20080306

• Dependence of the L-alanyl-L-alanine conformation on molecular charge determined from ab initio computations and NMR spectra.

  The journal of physical chemistry. B 20080214

• Evolution of a family of metazoan active-site-serine enzymes from penicillin-binding proteins: a novel facet of the bacterial legacy.

  BMC evolutionary biology 20080101

• Regulation of osmoadaptation in the moderate halophile Halobacillus halophilus: chloride, glutamate and switching osmolyte strategies.

  Saline systems 20080101

• Dynamic selection of novel vancomycin N-terminal derivatives by resin-bound reversed D-Ala-D-Ala.

  Journal of combinatorial chemistry 20080101

• The lantibiotic mersacidin is a strong inducer of the cell wall stress response of Staphylococcus aureus.

  BMC microbiology 20080101

• Phage display-derived inhibitor of the essential cell wall biosynthesis enzyme MurF.

  BMC biochemistry 20080101

• Usefulness of spectroscopy for biomedical engineering.

  Acta of bioengineering and biomechanics 20080101

• Rickettsia phylogenomics: unwinding the intricacies of obligate intracellular life.

  PloS one 20080101

• Current and novel antibiotics against resistant Gram-positive bacteria.

  Infection and drug resistance 20080101

• Dipeptide structure determination by vibrational circular dichroism combined with quantum chemistry calculations.

  Chemphyschem : a European journal of chemical physics and physical chemistry 20071022

• Reactions of peptidoglycan-mimetic beta-lactams with penicillin-binding proteins in vivo and in membranes.

  ACS chemical biology 20070921

• Recognition of 2-aminothiazole-4-acetic acid derivatives by the peptide transporters PEPT1 and PEPT2.

  European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences 20070901

• Role of insertion elements and yycFG in the development of decreased susceptibility to vancomycin in Staphylococcus aureus.

  International journal of medical microbiology : IJMM 20070701

• Proteome analysis of Paenibacillus polymyxa E681 affected by barley.

  Journal of microbiology and biotechnology 20070601

• A novel lantibiotic acting on bacterial cell wall synthesis produced by the uncommon actinomycete Planomonospora sp.

  Biochemistry 20070522

• Dalbavancin: a review.

  Drugs of today (Barcelona, Spain : 1998) 20070501

• Diazenedicarboxamides as inhibitors of D-alanine-D-alanine ligase (Ddl).

  Bioorganic & medicinal chemistry letters 20070401

• Single-molecule force spectroscopy and imaging of the vancomycin/D-Ala-D-Ala interaction.

  Nano letters 20070301

• Bacterial ligands generated in a phagosome are targets of the cytosolic innate immune system.

  PLoS pathogens 20070301

• Serial replica exchange.

  The journal of physical chemistry. B 20070215

• Replica exchange with dynamical scaling.

  The Journal of chemical physics 20070207

• From A to B in free energy space.

  The Journal of chemical physics 20070207

• Doubly resonant three-wave-mixing spectroscopy of a chiral coupled-chromophore system in solution: coherent two-dimensional optical activity spectroscopy.

  The Journal of chemical physics 20070207

• Thermostable ATP regeneration system using polyphosphate kinase from Thermosynechococcus elongatus BP-1 for D-amino acid dipeptide synthesis.

  Journal of bioscience and bioengineering 20070201

• Genetic diversity among Enterococcus faecalis.

  PloS one 20070101

• Design of inhibitors of the MurF enzyme of Streptococcus pneumoniae using docking, 3D-QSAR, and de Novo design.

  Journal of chemical information and modeling 20070101

• Multiple pathways in conformational transitions of the alanine dipeptide: an application of dynamic importance sampling.

  Journal of computational chemistry 20060801

• Total synthesis and evaluation of [Psi[CH2NH]Tpg4]vancomycin aglycon: reengineering vancomycin for dual D-Ala-D-Ala and D-Ala-D-Lac binding.

  Journal of the American Chemical Society 20060308

• Trends in antibiotic susceptibility patterns and epidemiology of MRSA isolates from several hospitals in Riyadh, Saudi Arabia.

  Annals of clinical microbiology and antimicrobials 20060101

• A complete set of NMR chemical shifts and spin-spin coupling constants for L-Alanyl-L-alanine zwitterion and analysis of its conformational behavior.

  Journal of the American Chemical Society 20051207

• Phosphinate, sulfonate, and sulfonamidate dipeptides as potential inhibitors of Escherichia coli aminopeptidase N.

  Bioorganic & medicinal chemistry letters 20051201

• X-ray crystallographic analysis of 6-aminohexanoate-dimer hydrolase: molecular basis for the birth of a nylon oligomer-degrading enzyme.

  The Journal of biological chemistry 20051125

• Can proteins and crystals self-catalyze methyl rotations?

  The journal of physical chemistry. B 20051103

• Reconciling observations of sequence-specific conformational propensities with the generic polymeric behavior of denatured proteins.

  Biochemistry 20050830

• Characterization of Chlamydia MurC-Ddl, a fusion protein exhibiting D-alanyl-D-alanine ligase activity involved in peptidoglycan synthesis and D-cycloserine sensitivity.

  Molecular microbiology 20050701

• Three-dimensional quantitative structure-activity relationship analyses of beta-lactam antibiotics and tripeptides as substrates of the mammalian H+/peptide cotransporter PEPT1.

  Journal of medicinal chemistry 20050630

• The D-methyl group in beta-lactamase evolution: evidence from the Y221G and GC1 mutants of the class C beta-lactamase of Enterobacter cloacae P99.

  Biochemistry 20050524

• Enhanced sensitivity and resolution in (1)H solid-state NMR spectroscopy of paramagnetic complexes under very fast magic angle spinning.

  Journal of the American Chemical Society 20050427

• Differential inhibition of Staphylococcus aureus PBP2 by glycopeptide antibiotics.

  Journal of the American Chemical Society 20050316

• Affinity capture using vancomycin-bound magnetic nanoparticles for the MALDI-MS analysis of bacteria.

  Analytical chemistry 20050315

• Crystal structures of complexes between the R61 DD-peptidase and peptidoglycan-mimetic beta-lactams: a non-covalent complex with a 'perfect penicillin'.

  Journal of molecular biology 20050121

• Anti-CD3 antibodies OKT3 and hOKT3gamma1(Ala-Ala) induce proliferation of T cells but impair expansion of alloreactive T cells; aspecifc T cell proliferation induced by anti-CD3 antibodies correlates with impaired expansion of alloreactive T cells.

  International immunopharmacology 20050101

• Existence of specific 'folds' in polyproline II ensembles of an 'unfolded'alanine peptide detected by molecular dynamics.

  Journal of the American Chemical Society 20041222

• Synchronized conformational fluctuations and binding site desolvation during molecular recognition.

  Biochemistry 20041214

• Molecular recognition remolds the self-assembly of hydrogelators and increases the elasticity of the hydrogel by 10(6)-fold.

  Journal of the American Chemical Society 20041124

• Solvation effects on alanine dipeptide: A MP2/cc-pVTZ//MP2/6-31G** study of (Phi, Psi) energy maps and conformers in the gas phase, ether, and water.

  Journal of computational chemistry 20041115

• Self-protection mechanism in D-cycloserine-producing Streptomyces lavendulae. Gene cloning, characterization, and kinetics of its alanine racemase and D-alanyl-D-alanine ligase, which are target enzymes of D-cycloserine.

  The Journal of biological chemistry 20041029

• First principles investigation of vancomycin and teicoplanin binding to bacterial cell wall termini.

  Journal of the American Chemical Society 20040714

• The perfect penicillin? Inhibition of a bacterial DD-peptidase by peptidoglycan-mimetic beta-lactams.

  Journal of the American Chemical Society 20040707

• Nosocomial infection with vancomycin-dependent enterococci.

  Emerging infectious diseases 20040701

• The non-polar solvent potential of mean force for the dimerization of alanine dipeptide: the role of solute-solvent van der Waals interactions.

  Biophysical chemistry 20040501

• Investigation of noncovalent interactions in deprotonated peptides: structural and energetic competition between aggregation and hydration.

  Journal of the American Chemical Society 20040317

• Role of solvent in determining conformational preferences of alanine dipeptide in water.

  Journal of the American Chemical Society 20040303

• Water molecule adsorption on protonated dipeptides.

  Journal of the American Chemical Society 20040204

• Improved treatment of the protein backbone in empirical force fields.

  Journal of the American Chemical Society 20040128

• Supramolecular hydrogels respond to ligand-receptor interaction.

  Journal of the American Chemical Society 20031112

• A six amino acid deletion, partially overlapping the VanSB G2 ATP-binding motif, leads to constitutive glycopeptide resistance in VanB-type Enterococcus faecium.

  Molecular microbiology 20031101

• Phenotypic characteristics and population genetics of Enterococcus faecalis cultured from patients in Tehran during 2000-2001.

  Canadian journal of microbiology 20031001

• New chromogenic dipeptide substrate for continuous assay of the D-alanyl-D-alanine dipeptidase VanX required for high-level vancomycin resistance.

  The journal of peptide research : official journal of the American Peptide Society 20030801

• Replica-exchange method using the generalized effective potential.

  Physical review letters 20030801

• Using bifunctional polymers presenting vancomycin and fluorescein groups to direct anti-fluorescein antibodies to self-assembled monolayers presenting d-alanine-d-alanine groups.

  Journal of the American Chemical Society 20030416

• Peptido- and glycocalixarenes: playing with hydrogen bonds around hydrophobic cavities.

  Accounts of chemical research 20030401

• On-column derivatization of the antibiotics teicoplanin and ristocetin coupled to affinity capillary electrophoresis.

  Electrophoresis 20030301

• Application of a real-time biosensor to detect bacteria in platelet concentrates.

  Biochemical and biophysical research communications 20030103

• A simple model for polyproline II structure in unfolded states of alanine-based peptides.

  Protein science : a publication of the Protein Society 20021001

• Structures of two kinetic intermediates reveal species specificity of penicillin-binding proteins.

  Journal of molecular biology 20020906

• Gas-phase reactions of charged phenyl radicals with neutral biomolecules evaporated by laser-induced acoustic desorption.

  Journal of the American Society for Mass Spectrometry 20020201

• Molecular cloning and functional characterisation of VanX, a D-alanyl-D-alanine dipeptidase from Streptomyces coelicolor A3(2).

  Research in microbiology 20020101

• Conformational preferences and vibrational frequency distributions of short peptides in relation to multidimensional infrared spectroscopy.

  Journal of the American Chemical Society 20011226

• Evaluation of the conformational propensities of peptide isosteres as a basis for selecting bioactive pseudopeptides.

  The journal of peptide research : official journal of the American Peptide Society 20011201

• A selectively deprotectable triazacyclophane scaffold for the construction of artificial receptors.

  Organic letters 20011101

• Perspective.

  Protein science : a publication of the Protein Society 20010801

• Direct measurement indicates a slow cis/trans isomerization at the secondary amide peptide bond of glycylglycine.

  Journal of the American Chemical Society 20010704

• Scaled quantum mechanical force field for alanyl-alanine peptide in solution.

  Biopolymers 20010501

• The effect of specific antibodies on the inhibition of leucocyte migration caused by staphylococcal peptidoglycan.

  Acta pathologica et microbiologica Scandinavica. Section B, Microbiology 19761001