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

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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.

Category
Azido Amino Acids
Catalog number
BAT-007747
CAS number
942518-29-8
Molecular Formula
C4H8N4O2·HCl
Molecular Weight
180.59
Nγ-Azido-L-2,4-diaminobutyric acid hydrochloride
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
Related CAS
120042-14-0 (free base)
Appearance
White crystalline powder
Purity
98-102% (Assay by titration)
Melting Point
143-148 °C
Storage
Store at 2-8 °C
Solubility
In H2O: 125 mg/mL (692.18 mM; Need ultrasonic)
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
InChI Key
MHHYJRIDKLZZEO-DFWYDOINSA-N
Canonical SMILES
C(CN=[N+]=[N-])C(C(=O)O)N.Cl
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.
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