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467359

Sigma-Aldrich

(S)-(−)-4-Amino-2-hydroxybutyric acid

96%

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About This Item

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

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.

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

467359-5G:
467359-BULK:
467359-VAR:
467359-25G:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCM0234
MKBX5423V
MKBS2677V
04916JH
13126HH

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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
Bentley, J.M. et al.
Journal of the Chemical Society. Chemical Communications, 231-231 (1995)
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)

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