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718610

Sigma-Aldrich

3-[(2-Boc-amino)acetamido]phenylboronic acid pinacol ester

97%

Synonym(s):

([3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylcarbamoyl]-methyl)carbamic acid tert-butyl ester, 3-[2-(tert-Butoxycarbonylamino)acetamido]phenylboronic acid pinacol ester, tert-Butyl([3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylcarbamoyl]methylcarbamate)

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About This Item

Empirical Formula (Hill Notation):
C19H29BN2O5
Molecular Weight:
376.25
MDL number:
MFCD16294500
UNSPSC Code:
12352103
PubChem Substance ID:
329763594
NACRES:
NA.22

Assay

97%

form

solid

mp

155-160 °C

functional group

amide
amine

SMILES string

CC(C)(C)OC(=O)NCC(=O)Nc1cccc(c1)B2OC(C)(C)C(C)(C)O2

InChI

1S/C19H29BN2O5/c1-17(2,3)25-16(24)21-12-15(23)22-14-10-8-9-13(11-14)20-26-18(4,5)19(6,7)27-20/h8-11H,12H2,1-7H3,(H,21,24)(H,22,23)

InChI key

IYTPRTWBNLJZLK-UHFFFAOYSA-N

Application

3-[(2-Boc-amino)acetamido]phenylboronic acid pinacol ester can be used to prepare a boronic acid-derived artificial receptor, which selectively binds to a neurotransmitter 3,4-dihydroxyphenylalanine (L-DOPA) in aqueous media and also inhibits the enzyme L-DOPA decarboxylase.

Storage Class Code

11 - Combustible Solids

WGK

nwg

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKBC5387

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Design, synthesis and evaluation of a boronic acid based artificial receptor for l-DOPA in aqueous media
Ueno H, et al.
Chemical Communications (Cambridge, England), 49(88), 10403-10405 (2013)

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