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B3770

Sigma-Aldrich

(+)-Biotinamidohexanoic acid hydrazide

≥90% (TLC), powder

Synonym(s):

(+)-Biotin-ε-aminocaproyl hydrazide, (+)-Biotin-X-hydrazide, (+)-Biotinamidocaproyl hydrazide, BACH, N-(+)-Biotinyl-6-aminohexanoic hydrazide

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About This Item

Empirical Formula (Hill Notation):
C16H29N5O3S
CAS Number:
109276-34-8
Molecular Weight:
371.50
MDL number:
MFCD00077659
UNSPSC Code:
12352125
eCl@ss:
34058011
PubChem Substance ID:
24891734
NACRES:
NC.07

Assay

≥90% (TLC)

form

powder

solubility

DMSO: 25 mg/mL

storage temp.

2-8°C

SMILES string

[H][C@]12CS[C@@H](CCCCC(=O)NCCCCCC(=O)NN)[C@@]1([H])NC(=O)N2

InChI

1S/C16H29N5O3S/c17-21-14(23)8-2-1-5-9-18-13(22)7-4-3-6-12-15-11(10-25-12)19-16(24)20-15/h11-12,15H,1-10,17H2,(H,18,22)(H,21,23)(H2,19,20,24)/t11-,12-,15-/m0/s1

InChI key

IJJWOSAXNHWBPR-HUBLWGQQSA-N

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Application

Biotinylation reagent with aminocaproic spacer for aldehyde groups (e.g., periodate-oxidized sugars) and carboxylic acids. Typically used for coupling to glycoproteins through the carbohydrate by hydrazone bond formation.

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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S Spiegel et al.
Journal of immunology (Baltimore, Md. : 1950), 127(2), 572-575 (1981-08-01)
Biotin hydrazide was attached covalently to the aldehyde groups produced by periodate oxidation of bovine brain gangliosides. These modified gangliosides were incorporated into mature rat thymocytes by incubation of the biotinyl gangliosides in the culture medium containing these cells. Avidin
Adelaide U P Hain et al.
Journal of medicinal chemistry, 57(11), 4521-4531 (2014-05-03)
Atg8 is a ubiquitin-like autophagy protein in eukaryotes that is covalently attached (lipidated) to the elongating autophagosomal membrane. Autophagy is increasingly appreciated as a target in diverse diseases from cancer to eukaryotic parasitic infections. Some of the autophagy machinery is
Nobuaki Higashi et al.
Biochemical and biophysical research communications, 520(1), 152-158 (2019-10-05)
We examined whether chondroitin sulfates (CSs) exert inhibitory effects on heparanase (Hpse), the sole endoglycosidase that cleaves heparan sulfate (HS) and heparin, which also stimulates chemokine production. Hpse-mediated degradation of HS was suppressed in the presence of glycosaminoglycans derived from
M B Rosenberg et al.
Journal of neurochemistry, 46(2), 641-648 (1986-02-01)
beta-nerve growth factor (NGF) was modified by biotinylation via carboxyl group substitution (C-bio-NGF) using biotin hydrazide and the coupling reagent 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide, under reaction conditions that yielded an average of 3 biotin additions per NGF subunit. NGF was also biotinylated through
Kimberly MacKay et al.
Briefings in functional genomics, 19(4), 292-308 (2020-05-01)
The advent of high-resolution chromosome conformation capture assays (such as 5C, Hi-C and Pore-C) has allowed for unprecedented sequence-level investigations into the structure-function relationship of the genome. In order to comprehensively understand this relationship, computational tools are required that utilize
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