515-94-6

Usage

Definition

ChEBI: A diamino acid that is alanine in which one of the hydrogens of the methyl group is replaced by an amino group.

InChI:InChI=1/C3H8N2O2/c4-1-2(5)3(6)7/h2H,1,4-5H2,(H,6,7)

Upstream product

• 600-05-5 2,3-dibromopropionic acid 
• 3981-36-0 3-chloro-DL-alanine 
• 7664-41-7 ammonia 
• 83855-20-3 Neopeptin A 
• 89850-65-7 (R)-2,3-bis-(2-chloro-acetylamino)-propionic acid 
• 1356449-87-0 calyxamide A 
• 1356449-88-1 calyxamide B 
• 75452-33-4 Boc-Dap(NH₂)-CONH₂ 
• 28843-11-0 (S)-(-)-2,3-Bis-(benzoylamino)-propionsaeure 
• 56012-66-9 (2,4-dioxo-hexahydro-pyrimidin-5-yl)-urea 
• 18635-43-3 2-(S)-benzyloxycarbonylamino-3-aminopropionic acid 
• 11116-31-7 bleomycin-A₂ 
• 35761-26-3 (S)-3-amino-2-(((benzyloxy)carbonyl)amino)propanoic acid 
• 56-84-8 L-Aspartic acid 

Downstream Products

• 2462-51-3 α-amino-β-guanidinopropionic acid 
• 515-94-6 (S)-2,3-diaminopropionic acid 
• 473-81-4 glyceric acid 
• 6542-88-7 aminoacetaldehyde 
• 107-15-3 ethylenediamine 
• 20610-20-2 2,3-Diaminopropionic acid methyl ester 
• 13368-86-0 1,2,5-thiadiazole-3-carboxylic acid 
• 124-38-9 carbon dioxide 
• 7664-41-7 ammonia 
• 123646-95-7 2-(toluene-4-sulfonylamino)-4,5-dihydro-1H-imidazole-4-carboxylic acid 
• 686259-72-3 C₄H₁₀N₂O₂ 
• 1483-07-4 L-2-Amino-3-ureido-propanoic acid 
• 88971-40-8 N^α,N^β-bis(t-butoxycarbonyl)-L-α,β-diaminopropionic acid 
• 28415-54-5 N^β-(benzyloxycarbonyl)-L-α,β-diaminopropionic acid 

Relevant academic research and scientific papers

Structures and Biosynthetic Pathway of Coprisamides C and D, 2-Alkenylcinnamic Acid-Containing Peptides from the Gut Bacterium of the Carrion Beetle Silpha perforata

Coprisamides C and D (1 and 2) were isolated from a gut bacterium, Micromonospora sp. UTJ3, of the carrion beetle Silpha perforata. Based on the combined analysis of UV, MS, and NMR spectral data, the planar structures of 1 and 2 were elucidated to be unreported derivatives of coprisamides A and B, cyclic depsipeptides bearing a 2-alkenylcinnamic acid unit and the unusual amino acids β-methylaspartic acid and 2,3-diaminopropanoic acid. The absolute configuration of 1 was determined using the advanced Marfey's method, phenylglycine methyl ester derivatization, and J-based configuration analysis. The biosynthetic gene clusters for the coprisamides were investigated based on genomic data from coprisamide-producing strains Micromonospora sp. UTJ3 and Streptomyces sp. SNU533. Coprisamide C (1) was active against the Mycobacterium tuberculosis mc26230 strain.

Unique polyhalogenated peptides from the marine sponge Ircinia sp.

Two new bromopyrrole peptides, haloirciniamide A (1) and seribunamide A (2), have been isolated from an Indonesian marine sponge of the genus Ircinia collected in the Thousand Islands (Indonesia). The planar structure of both compounds was assigned on the basis of extensive 1D and 2D NMR spectroscopy and mass spectrometry. The absolute configuration of the amino acid residues in 1 and 2 was determined by the application of Marfey's method. Compound 1 is the first dibromopyrrole cyclopeptide having a chlorohistidine ring, while compound 2 is a rare peptide possessing a tribromopyrrole ring. Both compounds failed to show significant cytotoxicity against four human tumor cell lines, and neither compound was able to inhibit the enzyme topoisomerase I or impair the interaction between programmed cell death protein PD1 and its ligand, PDL1.

Immunomodulatory peptides

The invention relates to peptides derivatized with a hydrophilic polymer which, in some embodiments, bind to human FcRn and inhibit binding of the Fc portion of an IgG to an FcRn, thereby modulating serum IgG levels. The disclosed compositions and methods may be used in some embodiments, for example, in treating autoimmune diseases and inflammatory disorders. The invention also relates, in further embodiments, to methods of using and methods of making the peptides of the invention.

Synthesis of L-2,3-diaminopropionic acid, a siderophore and antibiotic precursor

L-2,3-diaminopropionic acid (L-Dap) is an amino acid that is a precursor of antibiotics and staphyloferrin B a siderophore produced by Staphylococcus aureus. SbnA and SbnB are encoded by the staphyloferrin B biosynthetic gene cluster and are implicated in L-Dap biosynthesis. We demonstrate here that SbnA uses PLP and substrates O-phospho-L-serine and L-glutamate to produce a metabolite N-(1-amino-1-carboxyl-2-ethyl)-glutamic acid (ACEGA). SbnB is shown to use NAD+ to oxidatively hydrolyze ACEGA to yield α-ketoglutarate and L-Dap. Also, we describe crystal structures of SbnB in complex with NADH and ACEGA as well as with NAD+ and α-ketoglutarate to reveal the residues required for substrate binding, oxidation, and hydrolysis. SbnA and SbnB contribute to the iron sparing response of S. aureus that enables staphyloferrin B biosynthesis in the absence of an active tricarboxylic acid cycle.

CATIONIC LIPIDS, METHODS FOR PREPARING THE SAME, AND DELIVERY SYSTEMS HAVING ABILITY TO TRANSITION INTO CELLS COMPRISING THE SAME

The present invention provides cationic lipids, methods for preparing the same, and delivery systems comprising the same. The present invention can provide cationic lipids which enhance the efficiency of intracellular or in vivo delivery of multiple-anionic target compounds such as drugs, anticancer agents, nucleic acids, etc., have no intracellular toxicity, but show increased stability, methods for preparing the same, and delivery systems comprising the same.

Catalyst functional group cooperativity in the amino acid-catalysed nitroaldol condensation reaction

Several amino acids and their derivatives have been evaluated as organic catalysts for the nitroaldol reaction. It was found that when an unprotected amino group and an unprotected carboxylate group were present in the organocatalyst, both the nitroaldol reaction and subsequent elimination could occur to afford nitroalkenes from aromatic aldehydes and nitromethane. The best results were obtained by use of γ-amino acids derived from l-glutamine. It is suggested that the amino group is important for intermediate Schiff base formation and that the free carboxylate group facilitates the elimination step.

Total synthesis of nominal (11S)- and (11R)-cyclocinamide A

The cyclocinamides possess a unique β2αβ 2α 14-membered tetrapeptide core. The initially reported biological data and intriguing structure, which was without full stereochemical identification, necessitated synthesis of both nominal (all-S) cyclocinamide A and the 11R isomer. The completed synthesis is highlighted by the use of a (cyclo)asparagine-containing dipeptide as a turn inducing fragment. Due to inconsistencies in analytical data between natural and synthetic samples, a re-evaluation of the natural product stereochemistry appears necessary.

Calyxamides A and B, cytotoxic cyclic peptides from the marine sponge Discodermia calyx

Cyclic peptides containing 5-hydroxytryptophan and thiazole moieties were isolated from the marine sponge Discodermia calyx collected near Shikine-jima Island, Japan. The structures of calyxamides A (1) and B (2), including the absolute configurations of all amino acids, were elucidated by spectroscopic analyses and degradation experiments. The structures are similar to keramamides F and G, previously isolated from Theonella sp. The analysis of the 16S rDNA sequences obtained from the metagenomic DNA of D. calyx revealed the presence of Candidatus Entotheonella sp., an unculturable δ-proteobacterium inhabiting the Theonella genus and implicated in the biosynthesis of bioactive peptides.

Synthesis of cyclic guanidine intermediates of anatoxin-a(s) in both racemic and enantiomerically pure forms

The alkyl chain of anatoxin-a(s) (cyclic guanidines), which can be used as an intermediate in the total synthesis of anatoxin-a(s), was synthesized in both racemic and enantiomerically pure forms. These enantiomerically pure cyclic compounds can be used as chiral inductors in some reactions. The two racemic routes disclosed herein have the advantages of high overall yield and mild reaction conditions. Both routes proceed through an intermediate 2,3-diaminoacid - an important synthetic scaffold - with good yields. Furthermore, the N,N-dimethyl-2(tosylimino)imidazolidine-4-carboxamide might be obtained from 2-(tosylimino)imidazolidine-4-carboxylic acid followed by selective reduction of the carbonyl functionality. All synthesized compounds were analyzed by mass spectrometry and 1H NMR and 1C NMR spectroscopy. Georg Thieme Verlag Stuttgart - New York.

Process for producing alpha 2,3/ alpha 2,8-sialyltransferase and sialic acid-containing complex sugar

The present invention can provide a process for producing a protein having α2,3/α2,8-sialyltransferase activity using a transformant comprising a DNA encoding a protein having α2,3/α2,8-sialyltransferase activity derived from a microorganism belonging to the genus Pasteurella and a process for producing a sialic acid-containing complex carbohydrate using a transformant capable of producing a protein having α2,3/α2,8-sialyltransferase activity derived from a microorganism.