All Photos(2)
About This Item
Linear Formula:
H2NCH2CH2CH(OH)CO2H
CAS Number:
Molecular Weight:
119.12
Beilstein:
1721686
MDL number:
UNSPSC Code:
12352116
PubChem Substance ID:
EC Index Number:
670-305-7
NACRES:
NA.22
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Assay
96%
optical activity
[α]23/D −30°, c = 1 in H2O
mp
200-203 °C (lit.)
SMILES string
NCC[C@H](O)C(O)=O
InChI
1S/C4H9NO3/c5-2-1-3(6)4(7)8/h3,6H,1-2,5H2,(H,7,8)/t3-/m0/s1
InChI key
IVUOMFWNDGNLBJ-VKHMYHEASA-N
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General description
(S)-(-)-4-Amino-2-hydroxybutyric acid is an important moiety of butirosin, an aminoglycoside antibiotic.
Application
(S)-(-)-4-Amino-2-hydroxybutyric acid may be used in the preparation of 6′-amino-1-N-[(S)-4-amino-2-hydroxybutyryl]-6′-deoxylividomycin A.
Building block for enantiopure 3-hydroxypyrrolidin-2-ones.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.
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Bentley, J.M. et al.
Journal of the Chemical Society. Chemical Communications, 231-231 (1995)
Y Ota et al.
The Journal of antibiotics, 53(10), 1158-1167 (2001-01-02)
Butirosin is an interesting 2-deoxystreptamine (DOS)-containing aminoglycoside antibiotic produced by non-actinomycete Bacilli. Recently we were successful in purification of 2-deoxy-scyllo-inosose synthase from butirosin-producer Bacillus circulans as the key enzyme for the biosynthesis of DOS, in cloning of the responsible gene
Synthesis of 6'-Amino-1-N-[(S)-4-Amino-2-Hydroxybutyryl]-6'-Deoxylividomycin A.
Watanabe I, et al.
Bulletin of the Chemical Society of Japan, 48(8), 2303-2305 (1975)
M Philippe et al.
The Journal of antibiotics, 35(11), 1507-1512 (1982-11-01)
A semisynthetic aminoglycoside antibiotic 15, containing a cyclic gamma-amino-alpha-hydroxy acid, related to the 1-N-4-amino-2-hydroxybutyric acid (AHBA) side chain of butirosins and amikacin, has been prepared. Conveniently protected 3,2',6'-tris-N-tert-butoxycarbonylgentamicin C1a (12) was condensed with the phtalimido active ester 10 to give
Synthesis of (S)-Isoserine.
Miyazawa T, et al.
Agricultural and Biological Chemistry, 40(8), 1651-1652 (1976)
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