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

 CAS No.: 942518-29-8  Cat No.: BP-500029  Purity: 98-102% (Assay by titration) 4.5  

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.

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

Structure of 942518-29-8

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Molecular Formula
C4H8N4O2·HCl
Molecular Weight
180.59
Appearance
White crystalline powder

* For research and manufacturing use only. Not for human or clinical use.

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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.
IUPACName
(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
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
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.
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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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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