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467359

Sigma-Aldrich

(S)-(−)-4-Amino-2-hydroxybutyric acid

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About This Item

Linear Formula:
H2NCH2CH2CH(OH)CO2H
CAS Number:
40371-51-5
Molecular Weight:
119.12
Beilstein/REAXYS Number:
1721686
MDL number:
MFCD00674110
UNSPSC Code:
12352116
PubChem Substance ID:
24870402
EC Index Number:
670-305-7
NACRES:
NA.22

$22.50

List Price$45.00Save 50%
Web-Only Promotion
7 left in stockDetails
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Quality Level

100

assay

96%

optical activity

[α]23/D −30°, c = 1 in H2O

mp

200-203 °C (lit.)

functional group

amine
carboxylic acid
hydroxyl

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.[1]

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.[2]
Building block for enantiopure 3-hydroxypyrrolidin-2-ones.[3]

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKCM0234
MKBX5423V
MKBS2677V
04916JH
13126HH

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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 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)
Synthesis of (S)-Isoserine.
Miyazawa T, et al.
Agricultural and Biological Chemistry, 40(8), 1651-1652 (1976)
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

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