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SML1466

Sigma-Aldrich

ABH hydrochloride

≥98% (HPLC)

Synonym(s):

2(S)-Amino-6-boronohexanoic acid hydrochloride, 6-Borono-L-norleucine hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C6H14BNO4 · HCl
CAS Number:
194656-75-2
Molecular Weight:
211.45
MDL number:
MFCD22887376
UNSPSC Code:
12352200
PubChem Substance ID:
329825900
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D +8 to +13°, c = 0.7 in H2O

storage condition

desiccated

color

white to beige

solubility

H2O: 20 mg/mL, clear

storage temp.

2-8°C

SMILES string

OB(O)CCCC[C@H](N)C(O)=O.[H]Cl

InChI

1S/C6H14BNO4.ClH/c8-5(6(9)10)3-1-2-4-7(11)12;/h5,11-12H,1-4,8H2,(H,9,10);1H/t5-;/m0./s1

InChI key

XCUVEZUCSHVMRK-JEDNCBNOSA-N

Biochem/physiol Actions

ABH (2(S)-amino-6-boronohexanoic acid) is a highly potent and specific arginase inhibitor that inhibits the LPS-induced increases in pulmonary IL-8, neutrophils and goblet cells as well as airway fibrosis in rodent model of COPD.
Selective inhibition of arginase by ABH in animal models is known to ameliorate the effect of diabetes mellitus type 1, autoimmune encephalitis, chronic asthma and vascular stiffness due to aging. ABH inhibition of arginase restores erectile hemodynamics in aging mouse. Ex vivo studies prove that ABH promotes smooth muscle relaxation stimulated by nitric oxide.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Structure and function of arginases.
Ash D E.
The Journal of Nutrition, 134(10), 2760S-2764S (2004)
Chronic oral administration of the arginase inhibitor 2 (S)?amino?6?boronohexanoic acid (ABH) improves erectile function in aged rats.
Segal R, et al.
Journal of Andrology, 33(6), 1169-1175 (2012)
Yvonne Grobben et al.
Journal of structural biology: X, 4, 100014-100014 (2020-07-11)
Arginase-1 is a manganese-dependent metalloenzyme that catalyzes the hydrolysis of L-arginine into L-ornithine and urea. Arginase-1 is abundantly expressed by tumor-infiltrating myeloid cells that promote tumor immunosuppression, which is relieved by inhibition of Arginase-1. We have characterized the potencies of

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