Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
The examiner of record has changed to Richard Grant Peckham. Examiner can be reached at (703) 756-4621 during regular business hours (CST).
Detailed Action
Claims 1-22 are currently pending.
Election/Restriction
Applicant’s election with traverse of Group I (Claims 1-21, drawn to a method of modifying an oligopeptide, polypeptide, or protein) and the elected species of glutathione, sodium bicarbonate, DMSO, pentafluoropyridine, an Ir photocatalyst, and “enol acetate” (interpreted for examination to be the enol form of acetate:
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) in the reply filed on 8/25/2025 is acknowledged.
Claims 2, 5, 8, 10, 12-13, 15-17, and 22 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to nonelected Group II or unelected species, there being no allowable generic or linking claim. (Claim 2 is limited to a substituted aromatic “hydrocarbon”. Pyridine possesses a nitrogen ring member and is not a hydrocarbon. The formula of Claim 5 is limited to activating agents with only two substituents. The formulae of Claim 10 do not encompass “enol acetate”
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as elected.) Claims 1, 3-4, 6-7, 9, 11, 14, and 18-21 are being examined on the merits herein. Again, election was made with traverse in the reply filed on 8/25/2026.
Applicant argues that the required restriction/election is improper because examiner has not demonstrated a search burden and that Griffiths teaches an inefficient method with a different activating agent than those claimed (TCEP). However, applicant’s arguments are not persuasive as search burden is not a consideration for restriction requirement in the national stage of a 371 application. Further, efficiency or yield is not a consideration which can overcome anticipation by a reference under 35 USC 102. Further, Claim 1 does not restrict the activating agent to a particular subgenus; therefore, TCEP is an activating agent encompassed by Claim 1 and the common technical feature between groups is anticipated.
Thus, the requirement is deemed proper and is therefore made final.
A search using the elected species
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as the “active agent” yielded no prior art. The search was extended to “activating agents” comprising halo-substituted aromatic hydrocarbons.
Claim Objections
Claims 1, 3-4, 6-7, 9, 11, 14, 18-21 are objected to because of the following informalities:
Claims 1, 3-4, 6-7, 9, 11, 14, 18-21: “polypeptide and protein” as written in the preamble of the claim and S2 of Claim 1 and the preambles of the other listed claims should instead read “oligopeptide, polypeptide, or protein” as in S1 for clarity and consistency.
Claim 3: “in a middle of” should instead read “in the middle of”.
Appropriate correction is required.
Claim Rejections - 35 USC § 112(b)
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 4, 6, 9, 11, 18, and 21 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention.
Claims 4, 6, 11, and 18 all use the term “comprises” to precede a list of chemical alternatives. The term “comprises/ing” is open and not specifically limiting to the groups which follow the term. Therefore, it is suggested that applicant amend “comprises” (when used to precede a list of alternate chemical groups) to instead read “is selected from”.
Claims 9 and 21 recite the term “preferably”. It is unclear whether the limitations following the phrase are part of the claimed invention or merely exemplary. See MPEP § 2173.05(d).
Claim 4 recites “halogenoid” without further limitation. Halogenoid is not a recognized term in the art and applicant’s specification does not offer a limiting definition of the term. Page 6 describes potential embodiments of halogenoids, but the description uses non-limiting language like “as an embodiment” and “includes”. Therefore, the metes and bounds of the term and Claim 4 are indefinite.
Claim 4 recites “heteroaromatic hydrocarbon”. This phrase is a contradictory as both terms individually are mutually exclusive. A heteroaromatic ring is an aromatic ring in which at least one of the ring members are a heteroatom whereas a hydrocarbon is a chemical comprised entirely of hydrogen and carbon atoms, i.e., non-heteroatoms. Therefore, the cited term reflects two sets of metes and bounds, rendering the scope of the claim unclear.
Claim Rejections - 35 USC § 112(d)
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claims 3, 7, and 20 are rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends.
Claim 3 teaches modification of the C-, N-terminus, or middle of a peptide. All three parts comprise the whole peptide or protein. Therefore, the reaction of Claim 1 necessarily is performed at one of these locations and Claim 1 is not further limited.
Claim 7 lists the elected cycle
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, which is a heterocycle and not a hydrocarbon ring. Claim 7 depends on Claim 2 which limits the active agent to a hydrocarbon only. Therefore, Claim 7 improperly alters the scope of Claim 2.
Claim 20 requires the reaction is performed in the presence of “the photocatalyst and light”. Claim 1, upon which Claim 20 depends, already requires induction (through light) of a photocatalyst. Therefore, Claim 1 is not further limited by Claim 20.
Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claims 1, 3, 9, 11, 14, and 18-21 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Griffiths (Angew. Chem. Int. Ed. 2022, 61, e202110223).
Griffiths teaches the following reaction scheme on Page 2:
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wherein a peptide cysteine is reacted with a monosubstituted terminal olefin and an activating agent in the presence of blue light and an Ir photocatalyst resulting in the removal of SH through an EDA radical complex and addition of a new C-C bond and an amino functional group (Fig. 1). The reaction is performed in DMSO in an aqueous alkaline phosphate buffer solution (Page 2, Right Col.).
Claims 1, 3-4, 9, 11, 14, and 18-21 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Wang (Angew. Chem. Int. Ed. 2021, 60, 2155 – 2159).
Wang teaches the following reaction scheme on Page 2155:
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and exemplary olefin reactant:
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as the
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in Table 1 of Page 2156 wherein the reaction conditions are as follows:
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. An amino acid or peptide cysteine is reacted with a monosubstituted terminal olefin and an activating agent, which is a halo-substituted aromatic hydrocarbon
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, in the presence of blue light and an Ir photocatalyst resulting in the removal of SH through an EDA radical complex and addition of a new C-C bond and an ester functional group. The reaction is performed in DMSO in aqueous inorganic potassium thioacetate buffer solution.
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
Claims 1, 3, 9, 11, 14, and 18-21 are rejected under 35 U.S.C. 103 as being unpatentable over Griffiths (Angew. Chem. Int. Ed. 2022, 61, e202110223) in view of Hirayama (Journal of Chromatography A, 1369 (2014) 161–169), Lee (WO2020032622), and Oosthuizen (Redox Report, Vol. 6, No. 2, 2001 105-116).
Griffiths teaches the following reaction scheme on Page 2:
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wherein a peptide cysteine is reacted with a monosubstituted terminal olefin and an activating agent in the presence of blue light and an Ir photocatalyst resulting in the removal of SH through an EDA radical complex and addition of a new C-C bond and an amino functional group (Fig. 1). The reaction is performed in DMSO in an aqueous alkaline phosphate buffer solution (Page 2, Right Col.).
Griffiths does not teach using the elected olefin and peptide in the claimed reaction, nor does Griffiths teach sodium bicarbonate salt.
Hirayama teaches gamma-Glu-Glu-Gly
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, the end product of both elected reagents when reacted as instructed by Griffiths (Page 162, Table 1). The gamma-glutamyl tripeptide (oligo peptide) is a useful biomarker in serum samples (Abstract).
Lee teaches peptides including “γ-GLU-LEU-GLY”
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for antioxidant therapeutic use (Abstract; Page 35). The peptide can be formed as instructed by Griffiths from glutathione and propylene.
Oosthuizen teaches bicarbonate as an effective buffer ion and inorganic salt in radical EDA systems like those claimed and in Griffiths (Abstract; Page 110-111).
One of skill in the art seeking to form particular modified peptides like those taught in Hirayama and Lee would find it obvious to develop the peptides for their respective use (biomarker mass spectrometry calibration or antioxidant therapy) according to the reaction taught in Griffiths because Griffiths teaches “a visible-light-mediated desulfurative C(sp3)–C(sp3) bond forming reaction” through olefin-cysteine reaction before the effective filing date of the examined invention (Abstract). One would expect success in doing so because Griffiths broadly teaches the modifications for proteins post-translation and in small peptides. Similarly, Oosthuizen teaches similar functionality of the elected species of inorganic salt in radical chemical systems, rendering it as an obvious functional substitute to the other sodium buffer salt taught in Griffiths.
Claims 1, 3-4, 9, 11, 14, and 18-21 are rejected under 35 U.S.C. 103 as being unpatentable over Wang (Angew. Chem. Int. Ed. 2021, 60, 2155 – 2159) in view of Hirayama (Journal of Chromatography A, 1369 (2014) 161–169), Lee (WO2020032622), and Oosthuizen (Redox Report, Vol. 6, No. 2, 2001 105-116).
Wang teaches the following reaction scheme on Page 2155:
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and exemplary olefin reactant:
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as the
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in Table 1 of Page 2156 wherein the reaction conditions are as follows:
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. An amino acid or peptide cysteine is reacted with a monosubstituted terminal olefin and an activating agent, which is a halo-substituted aromatic hydrocarbon
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, in the presence of blue light and an Ir photocatalyst resulting in the removal of SH through an EDA radical complex and addition of a new C-C bond and an ester functional group. The reaction is performed in DMSO in aqueous inorganic potassium thioacetate buffer solution.
Wang does not teach using the elected olefin and peptide in the claimed reaction, nor does Wang teach sodium bicarbonate salt.
Hirayama teaches gamma-Glu-Glu-Gly
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, the end product of both elected reagents when reacted as instructed by Wang (Page 162, Table 1). The gamma-glutamyl tripeptide (oligo peptide) is a useful biomarker in serum samples (Abstract).
Lee teaches peptides including “γ-GLU-LEU-GLY”
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for antioxidant therapeutic use (Abstract; Page 35). The peptide can be formed as instructed by Wang from glutathione and propylene.
Oosthuizen teaches bicarbonate as an effective buffer ion and inorganic salt in radical EDA systems like those claimed and in Wang (Abstract; Page 110-111).
One of skill in the art seeking to form particular modified peptides like those taught in Hirayama and Lee would find it obvious to develop the peptides for their respective use (biomarker mass spectrometry calibration or antioxidant therapy) according to the reaction taught in Wang because Wang teaches “Conversion of C-S Bonds in Cysteine Derivatives into C-C Bonds” through olefin-cysteine reaction before the effective filing date of the examined invention (Title). One would expect success in doing so because Wang broadly teaches the modifications for diverse unnatural amino acids (which may comprise peptides of various length) and in small peptides (
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: Page 2155). Oosthuizen teaches similar functionality of the elected species of inorganic salt in radical chemical systems, rendering it as an obvious functional substitute to the other alkaline buffer salt taught in Wang.
Conclusion
No claim is allowable.
Inquiries
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Richard G. Peckham whose telephone number is (703)756-4621. The examiner can normally be reached 8:30am - 4:30pm EST.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Kortney Klinkel can be reached on (571) 270-5239. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/RICHARD GRANT PECKHAM/Examiner, Art Unit 1627
/Kortney L. Klinkel/Supervisory Patent Examiner, Art Unit 1627