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

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

Regulatory Information

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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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