Nγ-Azido-L-2,4-diaminobutyric acid hydrochloride - CAS 942518-29-8

Nγ-Azido-L-2,4-diaminobutyric acid hydrochloride is a modified amino acid used for the introduction of bioorthogonal handles into proteins. It is used in the synthetic preparation of glucosyl phosphine derivatives for site-selective traceless Staudinger ligation with azide containing proteins.

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Molecular Formula
C4H8N4O2·HCl
Molecular Weight
180.59

Nγ-Azido-L-2,4-diaminobutyric acid hydrochloride

    • Specification
      • Related CAS
        120042-14-0 (free base)
        Purity
        98-102% (Assay by titration)
        Solubility
        In H2O: 125 mg/mL (692.18 mM; Need ultrasonic)
        Appearance
        White crystalline powder
        Storage
        Store at 2-8 °C
        Shipping
        Room temperature in continental US; may vary elsewhere.
        IUPAC Name
        (2S)-2-amino-4-azidobutanoic acid;hydrochloride
        Synonyms
        L-Dab(N3)-OH HCl; (S)-2-Amino-4-azidobutanoic acid hydrochloride; L-Azidohomoalanine hydrochloride; (S)-2-Amino-4-azido-butanoic acid HCl; azidohomoalanine hydrochloride; (2S)-2-amino-4-azidobutanoic acid hydrochloride; Ng-Azido-L-2,4-diaminobutyric acid hydrochloride
    • Properties
      • Melting Point
        143-148 °C
        InChI Key
        MHHYJRIDKLZZEO-DFWYDOINSA-N
        InChI
        InChI=1S/C4H8N4O2.ClH/c5-3(4(9)10)1-2-7-8-6;/h3H,1-2,5H2,(H,9,10);1H/t3-;/m0./s1
        Canonical SMILES
        C(CN=[N+]=[N-])C(C(=O)O)N.Cl
    • Reference Reading
      • 1. Isolation of a new peptide antibiotic, permetin A, from Bacillus circulans
        Y Takahara, Y Takeuchi, I Komura, Y Hirose, S Murao J Antibiot (Tokyo). 1979 Feb;32(2):115-20. doi: 10.7164/antibiotics.32.115.
        Permetin A was purified from the culture filtrate of Bacillus circulans AJ 3902 by extraction with n-butanol, precipitation with sodium helianthate, CM-cellulose column chromatography and Sephadex LH-20 column chromatography. The compound was found to be a new peptide antibiotic containing 2,4-diaminobutyric acid (Dab), leucine, isoleucine, phenylalanine, valine, serine (in a molar ratio of 3:2:1:1:1:1) and a fatty acid. This antibiotic showed activity in vitro against Gram-negative, Gram-positive and some anaerobic bacteria.
        2. Isolation of a new antibiotic 333-25, related to antibiotic EM 49. (Studies on antibiotics from the genus Bacillus. XI)
        J Shoji, H Hinoo, Y Wakisaka, K Koizumi, M Mayama J Antibiot (Tokyo). 1976 May;29(5):516-20. doi: 10.7164/antibiotics.29.516.
        A new antibiotic, 333-25, active against Gram-positive and Gram-negative bacteria, was isolated from the culture broth of Bacillus circulans 333-25. The antibiotic is a basic acylpeptide containing 2,4-diaminobutyric acid (5), leucine (2), phenylalanine (1) and a fatty acid. It is closely related to antibiotic EM 49, but can be differentiated by chromatographic behaviour.
        3. Isolation of octapeptin D (studies on antibiotics from the genus Bacillus. XXVII)
        J Shoji, R Sakazaki, Y Wakisaka, K Koizumi, S Matsuura, H Miwa, M Mayama J Antibiot (Tokyo). 1980 Feb;33(2):182-5. doi: 10.7164/antibiotics.33.182.
        A new peptide antibiotic complex, named octapeptin D, was isolated from culture broth of a microorganism belonging to the genus Bacillus. The trihydrochloride of the antibiotic was obtained as a colorless powder, soluble in water and methanol. The empirical formula, C47H88N12O11.3HCl.H2O, was indicated by elemental analysis. Amino acid analysis on the acid hydrolyzate demonstrated the presence of 2,4-diaminobutyric acid (4 moles), serine (1 mole) and leucine (3 moles). Gas chromatographic analysis with the methylated product of the ethereal extract of the acid hydrolyzate revealed the presence of beta-hydroxy isodecanoic acid, beta-hydroxy decanoic acid, beta-hydroxy isoundecanoic acid and beta-hydroxyanteisoundecanoic acid. Octapeptin D is active against Gram-negative and Gram-positive bacteria in vitro and in vivo.
    • Preparing Stock Solutions
      • ConcentrationVolumeMass1 mg5 mg10 mg
        1 mM5.5374 mL27.6870 mL55.3741 mL
        5 mM1.1075 mL5.5374 mL11.0748 mL
        10 mM0.5537 mL2.7687 mL5.5374 mL
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