62234-40-6

Usage

Chemical Properties

White crystalline powder

Uses

N-alpha-Z-D-2,4-Diaminobutyric Acid

InChI:InChI=1/C12H16N2O4/c13-10(11(15)16)6-7-14-12(17)18-8-9-4-2-1-3-5-9/h1-5,10H,6-8,13H2,(H,14,17)(H,15,16)

Upstream product

• 2650-64-8 Cbz-L-Gln 
• 1155-62-0 N-benzyloxycarbonyl-L-glutamic acid 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 1758-80-1 L-2,4-diaminobutyrate 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 7733-29-1 Z-Orn(Boc)-OH 
• 54786-05-9 Z-A2bu(γPht)-OH 
• 151132-82-0 Nα-Z-Nγ-Fmoc-L-2,4-diaminobutyric acid 
• 366780-93-0 N_α-carbobenzyloxy-L-2-amino-4-acryloylaminobutyric acid 
• 182618-33-3 (S)-4-Amino-2-benzyloxycarbonylamino-butyric acid methyl ester 
• 49855-91-6 2--4--L-2,4-diaminobutyric acid 
• 851223-91-1 C₂₁H₃₀N₂O₃ 
• 1351168-80-3 tert-butyl 4-((S)-3-(benzyloxycarbonylamino)-2-oxopyrrolidin-1-yl)-3,3-dimethylpiperidine-1-carboxylate 
• 1264245-95-5 C₇H₈O₃S*C₁₅H₂₀N₂O₄ 
• 1758-80-1 L-2,4-diaminobutyrate 
• 366780-97-4 (N_α-carbobenzyloxy-L-2-amino-4-acryloylamino)butyrylglycine tert-butyl ester 
• 366781-01-3 (N_α-carbobenzyloxy-L-2-amino-4-acryloylamino)butyrylglycine 
• 124921-76-2 (2S)-4-Amino-2-(benzyloxycarbonylamino)butansaeure-benzylester 

Relevant academic research and scientific papers

(S)-2-methyl-1,4,5,6-tetrahydromethylpyrimidine-4-carboxylic acid synthesis method

The present invention relates to a (S)-2-methyl-1,4,5,6-tetrahydromethylpyrimidine-4-carboxylic acid synthesis method. According to the method, L-glutamine is used as a raw material, the alpha-amino of the L-glutamine is protected with a protection group, a decarbonylating agent is added, a Hofmann degradation reaction is performed to remove the carbonyl group attached to the remaining amino, the protection group is removed to obtain L-2,4-diaminobutyric acid, and finally the prepared L-2,4-diaminobutyric acid and trimethyl orthoacetate are subjected to a ring forming reaction to obtain the (S)-2-methyl-1,4,5,6-tetrahydromethylpyrimidine-4-carboxylic acid. Compared to the method in the prior art, the method of the present invention has the following characteristics that the chemical synthesis route is provided, the steps of the synthesis process are simple, the raw materials are easy to obtain, the product purity is high, and the method is suitable for large-scale industrial production.

COMPOSITIONS AND METHODS FOR THE TREATMENT OF BACTERIAL INFECTIONS

Compositions and methods for the treatment of bacterial infections include compounds containing dimers of cyclic heptapeptides. In particular, compounds can be used in the treatment of bacterial infections caused by Gram-negative bacteria.

Benzimidazole analogs of l-tryptophan are substrates and inhibitors of tryptophan indole lyase from Escherichia coli

Tryptophan indole lyase (TIL), an enzyme found in Escherichia coli and related enterobacteria, produces indole from l-tryptophan (l-Trp). Indole is a signaling molecule in bacteria, affecting biofilm formation, pathogenicity and antibiotic resistance. β-(Benzimidazol-1-yl)-l-alanine (BZI-Ala), 2-amino-4-(benzimidazol-1-yl)butyric acid (homo-BZI-Ala) and 2-amino-5-(benzimidazol-1-yl)pentanoic acid (bishomo-BZI-Ala) were synthesized and tested as substrates and inhibitors of TIL. BZI-Ala is a good substrate of TIL, with Km = 300 μm, kcat = 5.6 s-1 and kcat/Km = 1.9 × 104, similar to l-Trp. BZI-Ala is also a good substrate for H463F mutant TIL, which has very low activity with l-Trp. In contrast, homo-BZI-Ala was found to be a potent competitive inhibitor of TIL, with a Ki of 13.4 μm. However, the higher homolog, bishomo-BZI-Ala, was inactive as an inhibitor of TIL at a concentration of 600 μm, and is thus a much weaker inhibitor. The reaction of TIL with BZI-Ala was too fast to be observed in the stopped-flow spectrophotometer, and shows an aldimine intermediate in the steady state. However, H463F TIL shows equilibrating mixtures of aldimine and quinonoid complexes in the steady state. The spectra of the reaction of TIL with homo-BZI-Ala show a rapidly formed intermediate absorbing at 340 nm, probably a gem-diamine, that decays slowly to form a quinonoid complex absorbing at 494 nm. The potent binding of homo-BZI-Ala may be due to it being a 'bi-product' analog of the indole-α-aminoacrylate complex. These results demonstrate that an amino acid substrate may be converted to a potent inhibitor of TIL simply by homologation, which may be useful in the design of other potent TIL inhibitors. β-(Benzimidazol-1-yl)-l-alanine (BZI-Ala), 2-amino-4-(benzimidazol-1-yl) butyric acid (homo-BZI-Ala), and 2-amino-5-(benzimidazol-1-yl)pentanoic acid (bishomo-BZI-Ala) were synthesized and tested as substrates and inhibitors of tryptophan indole-lyase (TIL), an enzyme found in Escherichia coli and related enterobacteria. BZI-Ala is a good substrate of TIL, homo-BZI-Ala is a potent competitive inhibitor of TIL, with Ki of 13.4 μM, but bishomo-BZI-Ala, was inactive as an inhibitor of TIL. 2013 The Authors Journal compilation

Total synthesis of padanamides A and B

The first total syntheses of padanamides A and B have been achieved, unambiguously confirming their structures. The Royal Society of Chemistry.

An Improved Preparation of N2-tert-Butoxycarbonyl- and N 2-Benzyloxycarbonyl-(S)-2,4-diaminobutanoic Acids

Utilizing N-benzyloxycarbonyl- (1a) and N-tert-butoxycarbonyl-(S) -glutamine (1b), a highly efficient and practical method for the synthesis of N2-benzyloxycarbonyl- and N 2-tert-butoxycarbonyl-(S)-2,4-diamino-butanoic acids (2a and 2b) has been developed. Reaction of (S)-glutamine derivatives with iodosobenzene diacetate in a mixture of THF-water at 4°C afforded selectively protected (S)-2,4-diaminobutanoic acids in good yields.

Synthesis of dipeptide-bound epoxides and α,β-unsaturated amides as potential irreversible transglutaminase inhibitors

Herein we report the synthesis of 24 novel peptides as potential irreversible inactivators of transglutaminase (TGase). These peptides were designed to resemble Cbz-L-Gly, known to be a good TGase substrate, and to include either α,β-unsaturated amide groups or the corresponding epoxide groups. The side chain length of the amino acid residue bearing the inhibitor group was also varied in order to permit investigation of this effect. Copyright

Metal Chelating Amino Acids in the Design of Peptides and Proteins. Synthesis of Nα-Fmoc/But Protected Amino Acids Incorporating Aminodiacetic Acid Moiety.

The synthesis of Fmoc/But protected amino acid chelators 14, 15, 16 and 24 is described.With respect to their Boc/Bzl derivatives, the title compounds offer synthetic advantage: peptide Ac-Ada(1)-Ala3-Ada(1)-Ala4-Glu-Lys-NH2 was assembled by So

THE SYNTHESIS OF A Nγ-PHTHALYL-Nα-METHYL-α,γ-DIAMINOBUTYRYL CONGENER OF VIRGINIAMYCIN S1

A synthesis of (A2bu=α,γ-diaminobutyric acid) is reported using the very efficient coupling agent BOP-Cl (N,N'-bis(3-oxo-2-oxazolidinyl)phosphinic chloride) for imino acid peptide bond formation.The total yield is 11percent for the 5 coupling steps and one lactonization.The final step was a cyclization between residues 5 and 6, after (I) first t-Boc acidic deprotection with 85percent HCOOH of the linear precursor Z-Thr(Nα-Boc-Phg-O-)-D-Abu-Pro-MePhe-MeA2bu(γPht)-OBut followed by (ii) acidic saponification (Tfa) of the t-Bu ester.This sequence was found to be prerequisite, in view of the extreme lability of the 4-5 peptide bond under acidic conditions.