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12804

Sigma-Aldrich

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
Beilstein:
7328329
EC Number:
423-020-5
MDL number:
MFCD00075445
UNSPSC Code:
12352107
PubChem Substance ID:
57647025
NACRES:
NA.22

product name

HBTU, ≥98.0% (T)

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

storage temp.

2-8°C

SMILES string

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

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

InChI key

UQYZFNUUOSSNKT-UHFFFAOYSA-N

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General description

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

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H317

Hazard Classifications

Skin Sens. 1A

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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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
The uronium/guanidinium peptide coupling reagents: finally the true uronium salts.
Carpino LA, et al.
Angewandte Chemie (International Edition in English), 41(3), 441-445 (2002)
Héloise Boullet et al.
Molecules (Basel, Switzerland), 24(9) (2019-05-06)
Antimicrobial peptides (AMPs) are considered as potential therapeutic sources of future antibiotics because of their broad-spectrum activities and alternative mechanisms of action compared to conventional antibiotics. Although AMPs present considerable advantages over conventional antibiotics, their clinical and commercial development still
Mark Lommel et al.
Scientific reports, 8(1), 11753-11753 (2018-08-08)
Thrombospondins (TSPs) are multidomain glycoproteins with complex matricellular functions in tissue homeostasis and remodeling. We describe a novel role of TSP as a Wnt signaling target in the basal eumetazoan Hydra. Proteome analysis identified Hydra magnipapillata TSP (HmTSP) as a
Marc-Philipp Pfeil et al.
Scientific reports, 8(1), 14926-14926 (2018-10-10)
The spread of antimicrobial resistance stimulates discovery strategies that place emphasis on mechanisms circumventing the drawbacks of traditional antibiotics and on agents that hit multiple targets. Host defense peptides (HDPs) are promising candidates in this regard. Here we demonstrate that
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