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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/REAXYS Number:
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)

Quality Level

200

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

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

signalword

Warning

hcodes

H317

Hazard Classifications

Skin Sens. 1A

Storage Class

11 - Combustible Solids

wgk_germany

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
BCCG0843
BCCB6870
BCBW2651
BCBQ0174V
BCBL7887V

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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
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
Pritha Agarwalla et al.
Molecular therapy oncolytics, 3, 16020-16020 (2016-08-25)
Recent study has shown that N-end rule pathway, an ubiquitin dependent proteolytic system, counteracts cell death by degrading many antisurvival protein fragments like BCLxL, BRCA1, RIPK1, etc. Inhibition of the N-end rule pathway can lead to metabolic stabilization of proapoptotic
Small molecule approach to studying protein tyrosine phosphatase.
Kumar S, et al.
Methods, 35(1), 9-21 (2005)
One-step 18 F-labeling of peptides for positron emission tomography imaging using the SiFA methodology.
Wangler C, et al.
Nature Protocols, 7(11), 1946-1946 (2012)
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The special need of SPPS for rapid and highly efficient coupling reagents led to the development of several new reagents starting from BOP (Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate).

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Greener Chemistry: Methods and Products for Amide Bond Formation

Amide bonds are ubiquitous in both nature and industrial applications. They are vital to the structure and function of biological macromolecules and polymers. The importance of this functionality has resulted in numerous approaches to its formation, ranging from stoichiometric activation of carboxylic acids to more recent advances in catalytic amide bond formation.

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