13836-37-8

Basic information

• Product Name: Boc-Arg(Tos)-OH
• Synonyms: BOC-ARG(TOS);BOC-ARG(TOS)-OH;BOC-ARGININE(TOS)-OH;BOC-L ARGININE (TOS);BOC-L-ARGININE(TOSYL);BOC-L-ARG(TOS);BOC-L-ARG(TOS)-OH;BOC-L-ARG(TOS)-OH ETOAC
• CAS NO: 13836-37-8
• Molecular Formula: C₁₈H₂₈N₄O₆S
• Molecular Weight: 428.51
• EINECS: 237-549-2
• Product Categories: Amino Acid Derivatives;Amino Acids;Arginine [Arg, R];Boc-Amino Acids and Derivative;Boc-Amino acid series
• Mol File: 13836-37-8.mol

Chemical Properties

• Melting Point: ~90 °C (dec.)
• Appearance: White to off-white/Powder
• Density: 1.31 g/cm³
• Refractive Index: 1.575
• Storage Temp.: -15°C
• PKA: 3.95±0.21(Predicted)
• BRN: 2683538
• CAS DataBase Reference: Boc-Arg(Tos)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Boc-Arg(Tos)-OH(13836-37-8)
• EPA Substance Registry System: Boc-Arg(Tos)-OH(13836-37-8)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 13836-37-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Boc-Arg(Tos)-OH is used as a building block for the synthesis of various peptide-based drugs, targeting a wide range of therapeutic applications. Its role in peptide chemistry is crucial, as it allows for the creation of complex peptide structures with specific biological activities.
Used in Research and Development:
In the field of research and development, Boc-Arg(Tos)-OH serves as an essential component in the design and synthesis of novel peptides for scientific investigations. It is particularly useful in studying the structure-activity relationships of peptides and their interactions with biological targets.
Used in Diagnostic Applications:
Boc-Arg(Tos)-OH is also employed in the development of diagnostic tools, such as peptide-based assays and tests, which can help in the early detection and monitoring of various diseases and conditions.
Used in Cosmetics Industry:
In the cosmetics industry, Boc-Arg(Tos)-OH is used as a key ingredient in the formulation of peptide-based anti-aging products. These products aim to improve skin elasticity, reduce the appearance of fine lines and wrinkles, and promote overall skin health.
Used in Agricultural Applications:
Boc-Arg(Tos)-OH can also be utilized in the development of bioactive peptides with potential applications in the agricultural sector. These peptides can be used as natural alternatives to traditional chemical pesticides, offering a more environmentally friendly approach to crop protection and management.

InChI:InChI=1/C18H28N4O6S/c1-12-7-9-13(10-8-12)29(26,27)22-16(19)20-11-5-6-14(15(23)24)21-17(25)28-18(2,3)4/h7-10,14H,5-6,11H2,1-4H3,(H,21,25)(H,23,24)(H3,19,20,22)

Upstream product

• 2651-15-2 N-[bis(methylthio)methylene]-p-toluenesulfonamide 

Downstream Products

• 61543-20-2 Boc-Arg(Tos)-OBzl 
• 110392-41-1 Ac-L-Phe-L-Arg-NH₂ 
• 73995-36-5 Boc-Arg(Tos)-ONSu 
• 109530-61-2 Arg-Tyr(PO₃H₂)-Val-Phe 
• 32886-65-0 Boc-Arg(Tos)-Leu-OBzl 
• 123167-53-3 Boc-Arg(Tos)-Lys(2Cl-Z)-Asp(OcHex)-Val-Tyr(2Br-Z)-OPa 
• 103613-72-5 Boc-Arg(Tos)-MeArg(Tos)-D-Leu-NHEt 
• 140894-62-8 N^α-Boc-N^ω-tosylarginine N,O-dimethylamide 
• 125700-50-7 Boc-Arg(Tos)-Arg(Tos)-Leu-Asp(OcHex)-Arg(Tos)-Ile-Gly-OPac 
• 129279-84-1 Boc-Arg(Tos)-Tyr(BrZ)-OBzl 
• 130457-98-6 Boc-Arg(Tos)-Leu-Asp(OcHex)-Arg(Tos)-Ile-Gly-OPac 
• 103340-25-6 Boc-Arg(Tos)-Met-Asp(OcHex)-Arg(Tos)-Ile-Gly-OPac 
• 124-38-9 carbon dioxide 
• 126027-20-1 C₂₇H₃₅N₅O₉S 

Relevant articles and documents

A highly effective method for synthesis of N(ω)-substituted arginines as building blocks for Boc/Fmoc peptide chemistry

Chemically and optically pure N(ω)-substituted arginine derivatives were prepared with high yields in two steps, starting from N(α)-protected ornithine and ArSO2N=C(SMe)2. The compounds were applied to solid phase peptide synthesis using Boc as well as Fmoc chemistries.

Selective detachment of Boc-protected amino acids and peptides from Merrifield, PAM and Wang resins by trimethyltin hydroxide

We describe the development of a new non-acidolytic and non- nucleophilic method for the selective cleavage by trimethyltin hydroxide of amino acids and dipeptides at benzyl ester links attached to resins commonly used in peptide synthesis.

Stable polypeptides having c-AMP production enhancing activity and the use thereof

Disclosed are (1) a polypeptide represented by formula (I), or a pharmaceutically acceptable amide, ester or salt thereof: wherein X is hydrogen atom; or a lower alkyl group which may be substituted with a member selected from the group consisting of hydroxy group, substituted or unsubstituted amino group, carboxyl group, carbamoyl group, and substituted or unsubstituted aromatic group; and Y is one of amino acids or peptides consisting of 1 to 16 amino acid residues counted from the N-terminal side of Leu-Ala-Ala-Val-Leu-Gly-Lys-Arg-Tyr-Lys-Gln-Arg-Val-Lys-Asn-Lys SEQ ID NO: 20, and (2) a pharmaceutical composition comprising a polypeptide represented by formula (I), or a pharmaceutically acceptable amide, ester or salt thereof, which has remarkable c-AMP activity and is useful as a nerve activating agent.

HIV related peptides

Fragments of HIV p17 protein ranging in length from about 12 to abut 40 amino acids are used to form diagnostics and vaccines for detection or treatment of AIDS. Specific peptide fragments extend from the N-terminal to the C-terminal. Peptides having the amino acid sequences shown by the following formula (I), (II), (III), (IV) and (V):, Tyr-Ser-Val-His-Gln-Arg-Ile-Asp-Val-Lys--Asp-Thr-Lys-Glu-Ala-Leu-Gly-Lys-Ile-Glu--Glu-Glu-Gln-Asn-Lys-Ser-Lys-Lys-Lys-Ala (I), Gly-Ala-Arg-Ala-Ser-Val-Leu-Ser-Gly-Gly--Glu-Leu-Asp-Arg-Trp-Glu-Lys-Ile-Arg-Leu--Arg-Pro-Gly-Gly-Lys-Lys-Lys-Tyr-Lys-Leu--Lys-His (II), Ile-Val-Trp-Ala-Ser-Arg-Glu-Leu-Glu-Arg--Phe-Ala-Val-Asn-Pro-Gly-Leu-Leu (III), Glu-Thr-Ser-Glu-Gly-Cys-Arg-Gln-Ile-Leu--Gly-Gln-Leu-Gln-Pro-Ser-Leu-Gln-Thr-Gly--Ser-Glu-Glu-Leu-Arg-Ser-Leu-Tyr-Asn-Thr--Val-Ala-Thr-Leu (IV), Ala-Gln-Gln-Ala-Ala-Ala-Asp-Thr-Gly-His--Ser-Ser-Gln-Val-Ser-Gln-Asn-Tyr (V), are immunoreactive to antibodies in sera of patients testing seropositive for p17 of HIV-1.

Antigen determinant peptides and a process for the preparation thereof

Antigen determinant peptides of the general formula I, H - Val - X - Y (I), in which X represents an octapeptidic to undecapeptidic sequence of a defined structure, Tyr-Tyr-Arg-Asp-Ser-Arg-Asn-Pro-Leu,Phe-Ile-His-Asn-Phe-Lys-Arg-Lys-Gly,Val-Pro-Arg-Arg-Lys-Ala-Lys-Ile,Leu-His-Thr-Gly-Glu-Arg-Asp-Trp-His-Leu-Gly,Ser-Gly-Lys-Ala-Arg-Gly-Trp-Phe, or Ser-Ile-Glu-Trp-Arg-Lys-Lys-Arg-Tyr-Ser, and Y stands for a hydroxyl or an amino group,available by fragment synthesis or successive condensation of the respective amino acid residues (stepwise build-up) in solution or on a solid carrier, are expected to be of use as diagnostic agents for the so-called acquired immunodeficiency syndrome (AIDS), and also to have a potential as monodeterminant antibodies and safe synthetic vaccine agents combating the human T-cell lymphotropic type III virus (HTLV-III, HIV).

Antigenic peptide compounds

The novel antigenic peptide compounds of this invention comprise sequences of 12 to 19 amino acids, which include twelve amino acid sequence glutamic acid-glutamine-leucine-isoleucine-glutamine-asparagine-leucine-valine-proline-glutamic acid-aspartic acid-lysine, all of the amino acids being in their L-forms. The compounds have utility in vaccines for reducing the fertility of mammals.

Peptides related to somatostatin

Peptides of the formula: STR1 wherein: X is H, --NH2, --NH--Gly--Ala, --NH--D--Ala--Ala, --NH--Gly--Gly--Gly, --NH--acetyl, or --NH--benzoyl; X1 is His or Arg; X2 is His, Glu, Tyr, Trp, or Phe; X3 is Trp, D-Trp, or 6-F-D-Trp; and X4 is a D-α-amino acid; or the reduced, linear form thereof, or a non-toxic, pharmaceutically acceptable acid addition salt thereof; inhibit the release of growth hormone, insulin, and glucagon; and show prolonged inhibition activity. Said peptides are prepared by solid-state methodology.

Polypeptides related to somatostatin

Compounds of the formula: STR1 wherein: X is H, Ala-Gly, Gly-Gly-Gly, Ala-D-Ala, acetyl, or benzoyl; X1 is Arg or His; X2 is Glu or Asp; X3 is Trp or D-Trp; or 6-F-D-Trp; and X4 is Cys- or D-Cys; or a non-toxic pharmaceutically acceptable acid addition salt thereof; inhibit the secretion of growth hormone and glucagon without materially affecting the secretion of insulin.

Novel decapeptide amide analogs of leuteinizing hormone-releasing hormone

The novel decapeptide amide derivatives of the formula wherein R1 is Tyr or Phe; R2 is D-Nle, D-Nva, D-Abu, D-Phe, D-Ser, D-Thr or D-Met and R3 is Leu, Ile or Nle have a strong ovulation inducing activity.