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Merck

12804

HBTU

≥98.0% (T), for peptide synthesis

Synonym(s):

N,N,N′,N′-Tetramethyl-O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate, O-(Benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate

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About This Item

Empirical Formula (Hill Notation):
C11H16F6N5OP
CAS Number:
94790-37-1
Molecular Weight:
379.24
NACRES:
NA.22
PubChem Substance ID:
57647025
UNSPSC Code:
12352107
EC Number:
423-020-5
MDL number:
MFCD00075445
Beilstein/REAXYS Number:
7328329

Key Documents

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Product Name

HBTU, ≥98.0% (T)

InChI key

UQYZFNUUOSSNKT-UHFFFAOYSA-N

InChI

1S/C11H16N5O.F6P/c1-14(2)11(15(3)4)17-16-10-8-6-5-7-9(10)12-13-16;1-7(2,3,4,5)6/h5-8H,1-4H3;/q+1;-1

SMILES string

F[P-](F)(F)(F)(F)F.CN(C)C(\On1nnc2ccccc12)=[N+](/C)C

assay

≥98.0% (T)

form

solid

reaction suitability

reaction type: Coupling Reactions

mp

200 °C (dec.) (lit.)

solubility

acetonitrile: 0.1 g/mL, clear

application(s)

peptide synthesis

functional group

amine

storage temp.

2-8°C

Quality Level

200

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Application

HBTU is a peptide coupling agent for peptide synthesis. It has also been used in standard Fmoc-based solid-phase peptide synthesis (SPPS) protocol.
Recent studies show that crystal as well as solution structure of this coupling agent is a guanidinium N-oxide and not an uronium compound; Coupling reagent for peptide synthesis; advantages are: very low racemization, simple reaction conditions, very short reaction time, and high yields.

General description

HBTU is a peptide coupling agent used in Fmoc-based solid-phase peptide synthesis.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H317

Hazard Classifications

Skin Sens. 1A

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF7285V
WXBF7035V
BCCH7947
BCCG0843
BCCB6870

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Kaido Kurrikoff et al.
Scientific reports, 7(1), 17056-17056 (2017-12-08)
Non-viral gene delivery systems have gained considerable attention as a promising alternative to viral delivery to treat diseases associated with aberrant gene expression. However, regardless of extensive research, only a little is known about the parameters that underline in vivo
Allan Bastos Lima et al.
Bioorganic & medicinal chemistry, 23(17), 5748-5755 (2015-08-04)
Dengue virus (DENV) and West Nile virus (WNV) are mosquito-borne arboviruses responsible for causing acute systemic diseases and severe health conditions in humans. The discovery of therapies capable to prevent infections or treat infected individuals remains an important challenge, since
Structural studies of reagents for peptide bond formation: Crystal and molecular structures of HBTU and HATU.
Abdelmoty I, et al.
Lett. Pept. Sci., 1(2), 57-67 (1994)
L P Miranda et al.
Proceedings of the National Academy of Sciences of the United States of America, 96(4), 1181-1186 (1999-02-17)
The chemical synthesis of peptides and small proteins is a powerful complementary strategy to recombinant protein overexpression and is widely used in structural biology, immunology, protein engineering, and biomedical research. Despite considerable improvements in the fidelity of peptide chain assembly
Hiroshi Wada et al.
PloS one, 13(7), e0199249-e0199249 (2018-07-04)
Recently, many autologous tumor antigens have been examined for their potential use in cancer immunotherapy. However, the success of cancer vaccines in clinical trials has been limited, partly because of the limitations of using single, short peptides in most attempts.
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