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P7739

Sigma-Aldrich

Protein kinase A inhibitor fragment 5-24 amide trifluoroacetate salt

≥95% (HPLC), lyophilized powder

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About This Item

MDL number:
MFCD03788008
UNSPSC Code:
41106305
PubChem Substance ID:
329820315
NACRES:
NA.32

Quality Level

200

Assay

≥95% (HPLC)

form

lyophilized powder

mol wt

calculated mol wt 2219

composition

Peptide content, ~75%

solubility

H2O: soluble

UniProt accession no.

P61925

shipped in

wet ice

storage temp.

−20°C

SMILES string

OC(=O)C(F)(F)F.CC[C@H](C)[C@H](NC(=O)[C@H](C)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=N)NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)[C@@H](NC(=O)[C@@H](N)[C@@H](C)O)[C@@H](C)O)[C@@H](C)CC)[C@@H](C)O)C(=O)N[C@@H](Cc3c[nH]cn3)C(=O)N[C@@H](CC(O)=O)C(N)=O

InChI

1S/C94H149N33O30.C2HF3O2/c1-11-42(3)70(125-86(152)59(31-50-19-14-13-15-20-50)119-85(151)62(36-68(138)139)118-75(141)44(5)111-82(148)58(32-51-24-26-53(132)27-25-51)121-91(157)73(49(10)131)127-87(153)69(96)47(8)129)89(155)113-45(6)76(142)123-63(40-128)78(144)108-38-65(134)115-55(22-17-29-106-93(100)101)81(147)126-72(48(9)130)88(154)109-39-66(135)114-54(21-16-28-105-92(98)99)79(145)116-56(23-18-30-107-94(102)103)80(146)120-61(34-64(95)133)83(149)112-46(7)77(143)124-71(43(4)12-2)90(156)122-60(33-52-37-104-41-110-52)84(150)117-57(74(97)140)35-67(136)137;3-2(4,5)1(6)7/h13-15,19-20,24-27,37,41-49,54-63,69-73,128-132H,11-12,16-18,21-23,28-36,38-40,96H2,1-10H3,(H2,95,133)(H2,97,140)(H,104,110)(H,108,144)(H,109,154)(H,111,148)(H,112,149)(H,113,155)(H,114,135)(H,115,134)(H,116,145)(H,117,150)(H,118,141)(H,119,151)(H,120,146)(H,121,157)(H,122,156)(H,123,142)(H,124,143)(H,125,152)(H,126,147)(H,127,153)(H,136,137)(H,138,139)(H4,98,99,105)(H4,100,101,106)(H4,102,103,107);(H,6,7)/t42-,43-,44-,45-,46-,47+,48+,49+,54-,55-,56-,57-,58-,59-,60-,61-,62-,63-,69-,70-,71-,72-,73-;/m0./s1

InChI key

CJBPFVMGYBOAOJ-AYVQDJQPSA-N

Gene Information

human ... PKIA(5569)

Amino Acid Sequence

Thr-Thr-Tyr-Ala-Asp-Phe-Ile-Ala-Ser-Gly-Arg-Thr-Gly-Arg-Arg-Asn-Ala-Ile-His-Asp-NH2

General description

Protein kinase A inhibitor fragment inhibits the protein kinase cAMP-activated catalytic subunit alpha (PRKACA). The gene encoding it is localized on human chromosome 19p13.1. Mutations in the gene encoding protein kinase cAMP-activated catalytic subunit α (PRKACA) have been associated with Cushing′s syndrome.

Biochem/physiol Actions

Binds to the catalytic subunit of protein kinase A (PKA), mimicking the protein substrate

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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The gene encoding the catalytic subunit Ca of cAMP-dependent protein kinase (locus PRKACA) localizes to human chromosome region 19p13. 1
Kjetil T
Genomics (1996)
Barbara Wienen-Schmidt et al.
ChemMedChem, 13(18), 1988-1996 (2018-07-31)
A ligand-binding study is presented focusing on thermodynamics of fragment expansion. The binding of four compounds with increasing molecular weight to protein kinase A (PKA) was analyzed. The ligands display affinities between low-micromolar to nanomolar potency despite their low molecular weight.
Activating hotspot L205R mutation in PRKACA and adrenal Cushing's syndrome.
Cao Y
Science (2014)
Barbara Wienen-Schmidt et al.
ChemMedChem, 16(1), 292-300 (2020-10-09)
In lead optimization, protein crystallography is an indispensable tool to analyze drug binding. Binding modes and non-covalent interaction inventories are essential to design follow-up synthesis candidates. Two protocols are commonly applied to produce protein-ligand complexes: cocrystallization and soaking. Because of
Humberto Muzi-Filho et al.
Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology, 54(6), 1143-1162 (2020-11-18)
Chronic malnutrition (M) affects >1 billion people worldwide. Epidemiological data point to long-term renal and cardiovascular outcomes (e.g. arterial hypertension, cardiorenal syndromes). The renin-angiotensin-aldosterone system (RAAS) has been implicated in the physiopathology of these disturbances, but M-induced alterations in RAAS-modulated

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