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379093

Sigma-Aldrich

(S)-(+)-2-Hydroxy-3-methylbutyric acid

99%, optical purity ee: 99% (GLC)

Synonym(s):

L-α-Hydroxyisovaleric acid

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About This Item

Linear Formula:
(CH3)2CHCH(OH)CO2H
CAS Number:
17407-55-5
Molecular Weight:
118.13
Beilstein:
1721140
MDL number:
MFCD00066443
UNSPSC Code:
51113400
PubChem Substance ID:
24863611
NACRES:
NA.22

Quality Level

200

Assay

99%

form

solid

optical activity

[α]20/D +19°, c = 1 in chloroform

optical purity

ee: 99% (GLC)

bp

124-125 °C/13 mmHg (lit.)

mp

68-70 °C (lit.)

SMILES string

CC(C)[C@H](O)C(O)=O

InChI

1S/C5H10O3/c1-3(2)4(6)5(7)8/h3-4,6H,1-2H3,(H,7,8)/t4-/m0/s1

InChI key

NGEWQZIDQIYUNV-BYPYZUCNSA-N

Related Categories

Application

A useful chiral building block for peptide synthesis. Used in the preparation of the cytotoxic didemnin cyclopeptides and of the antineoplastic agent dolastatin 15.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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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Journal of the American Chemical Society, 112, 7659-7659 (1990)
Pettit, G.R. et al.
Journal of the American Chemical Society, 113, 6692-6692 (1991)
Schmidt, U. et al.
Synthesis, 294-294 (1991)
O Arad et al.
Biopolymers, 29(12-13), 1633-1649 (1990-10-01)
Depsipeptide analogues of peptide sequences can help in elucidating the role of specific hydrogen bonds in determining the conformation in peptides. The repeating pentapeptide and hexapeptide sequences of elastin have been suggested to contain a type II beta-turn with a
A Haese et al.
Journal of molecular biology, 243(1), 116-122 (1994-10-14)
Enniatin synthetase catalyzes the biosynthesis of N-methylated cyclohexadepsipeptides. The 347 kDa enzyme is encoded by the esyn1 gene of Fusarium scirpi and contains two domains (EA and EB) homologous to each other and to regions of other microbial peptide synthetases.
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